Methyl 2-(2-{[(benz­yloxy)carbon­yl]amino}­propan-2-yl)-5-hy­droxy-6-oxo-1,6-dihydro­pyrimidine-4-carboxyl­ate

Shang, Z.; Ha, J.; Yu, Y.; Zhao, X.

doi:10.1107/S1600536811016278

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1336

doi:10.1107/S1600536811016278

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Methyl 2-(2-{[(benzyloxy)carbonyl]amino}propan-2-yl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate

Zhenhua Shang,^a ^* Jing Ha,^a Yifeng Yu ^a and Xiaodan Zhao ^a

^aCollege of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology, Shijiazhuang 050018, People's Republic of China
^*Correspondence e-mail: zhenhuashang@yahoo.com.cn

(Received 20 March 2011; accepted 29 April 2011; online 7 May 2011)

In the title compound, C₁₇H₁₉N₃O₆, the dihedral angle between the two aromatic rings is 45.9 (1)°. The crystal structure is stabilized through intermolecular N—H⋯O hydrogen bonds and intramolecular O—H⋯O hydrogen bonds are also present.

Related literature

For related structures, see: Fun et al. (2009 ); Shang & Shang (2007 ). The title compound is an intermediate in the preparation of the antiretroviral drug raltegravir [systematic name N-(2-(4-(4-fluorobenzylcarbamoyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)propan-2-yl)-5-methyl-1,3,4-oxadiazole-2-carboxamide. For therapeutic details of raltegravir, see Steigbigel et al. (2008 ). For synthetic details, see: Culbertson (1979 ).

Experimental

Crystal data

C₁₇H₁₉N₃O₆
M_r = 361.35
Monoclinic, P 2₁ /c
a = 12.122 (2) Å
b = 16.300 (3) Å
c = 9.1766 (18) Å
β = 106.29 (3)°
V = 1740.4 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 113 K
0.24 × 0.20 × 0.16 mm

Data collection

Bruker SMART diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.975, T_max = 0.983
15564 measured reflections
4142 independent reflections
3386 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.103
S = 1.09
4142 reflections
250 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O5ⁱ	0.882 (15)	2.133 (15)	2.8911 (14)	143.7 (12)
N2—H2⋯O2ⁱⁱ	0.938 (16)	1.886 (16)	2.8135 (16)	169.3 (13)
O1—H1⋯O3	0.918 (17)	1.788 (17)	2.6163 (14)	148.7 (16)
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z+2.

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811016278/wn2426sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811016278/wn2426Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811016278/wn2426Isup3.cml

checkCIF report

Comment top

Raltegravir (MK-0518, brand name Isentress), an antiretroviral drug produced by Merck & Co, is used to treat HIV infection (Steigbigel et al., 2008). It received FDA approval in October 2007, the first of a new class of HIV drugs, the integrase inhibitors, to receive such approval. The title compound is a key intermediate in the preparation of Raltegravir.

The pyrimidinone ring is planar, as it is in a related compound (Fun et al., 2009). This is in contrast with another related compound (Shang et al., 2007), where the heterocyclic ring is twisted. In the title compound the dihedral angle between the two aromatic rings is 45.9 (1)°. The crystal structure is stabilized through intermolecular N—H···O hydrogen bonds; intramolecular O—H···O hydrogen bonds are also present.

Related literature top

For related structures, see: Fun et al. (2009); Shang & Shang (2007). The title compound is an intermediate in the preparation of the antiretroviral drug raltegravir [systematic name N-(2-(4-(4-fluorobenzylcarbamoyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)propan-2-yl)-5-methyl-1,3,4-oxadiazole-2-carboxamide. For therapeutic details of raltegravir, see Steigbigel et al. (2008). For synthetic details, see: Culbertson (1979).

Experimental top

The title compound was prepared by a published method (Culbertson, 1979). To a slurry of benzyl 1-amino-1-(hydroxyimino)-2-methylpropan-2-ylcarbamate (2.9 g) in methanol (12 ml) was added dimethyl acetylenedicarboxylate (1.77 g) slowly at room temperature. After 1.5 h, the mixture was added to xylene (20 ml). The reaction mixture was then heated to reflux for 2 h and cooled to 60 °C. Methyl tert-butyl ether (9 ml) was added slowly to build a seed bed. The batch was then cooled to 0 °C for 14 h, and then further cooled to -5 °C and allowed to stand for 1 h before filtration. The solid was washed with methyl tert-butyl ether (4 ml) and dried. 50 mg of the title compound was dissolved in 30 ml methanol and the solution was kept at room temperature for 10 d. Natural evaporation gave colorless single crystals of the title compound which were suitable for X-ray analysis.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, drawn with 30% probability ellipsoids. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. The packing of the title compound,viewed down the a axis. The dashed lines indicate the hydrogen bonds.
	Fig. 3. The formation of the title compound.

Methyl 2-(2-{[(benzyloxy)carbonyl]amino}propan-2-yl)-5-hydroxy- 6-oxo-1,6-dihydropyrimidine-4-carboxylate top

Crystal data top

C₁₇H₁₉N₃O₆	D_x = 1.379 Mg m⁻³
M_r = 361.35	Melting point = 183–185 K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.122 (2) Å	Cell parameters from 4990 reflections
b = 16.300 (3) Å	θ = 2.5–27.9°
c = 9.1766 (18) Å	µ = 0.11 mm⁻¹
β = 106.29 (3)°	T = 113 K
V = 1740.4 (6) Å³	Plate, colorless
Z = 4	0.24 × 0.20 × 0.16 mm
F(000) = 760

Data collection top

Bruker SMART diffractometer	4142 independent reflections
Radiation source: rotating anode	3386 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.035
ω scans	θ_max = 27.9°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −15→15
T_min = 0.975, T_max = 0.983	k = −21→18
15564 measured reflections	l = −11→12

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0539P)² + 0.1964P] where P = (F_o² + 2F_c²)/3
4142 reflections	(Δ/σ)_max = 0.001
250 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₇H₁₉N₃O₆	V = 1740.4 (6) Å³
M_r = 361.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.122 (2) Å	µ = 0.11 mm⁻¹
b = 16.300 (3) Å	T = 113 K
c = 9.1766 (18) Å	0.24 × 0.20 × 0.16 mm
β = 106.29 (3)°

Data collection top

Bruker SMART diffractometer	4142 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	3386 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.983	R_int = 0.035
15564 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.33 e Å⁻³
4142 reflections	Δρ_min = −0.24 e Å⁻³
250 parameters

Special details top

Experimental. 1H-NMR (500 MHz, DMSO) 1.51(s, 6H), 3.82(s, 3H), 4.98(s, 2H), 7.35(bs, 5H), 7.45 (s, 1H), 10.24(s, 1H), 12.58(s, 1H)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.18567 (8)	0.11941 (5)	0.81459 (10)	0.0159 (2)
N2	0.36822 (8)	0.06461 (6)	0.92786 (11)	0.0179 (2)
N3	0.39582 (8)	0.18366 (6)	1.15086 (11)	0.0170 (2)
O1	0.28432 (8)	−0.00917 (5)	0.54614 (9)	0.0247 (2)
O2	0.45987 (7)	−0.02265 (5)	0.80609 (9)	0.0282 (2)
O3	0.08230 (7)	0.05655 (5)	0.42611 (9)	0.0234 (2)
O4	0.01176 (7)	0.14406 (5)	0.56692 (9)	0.01951 (19)
O5	0.40819 (7)	0.26902 (6)	0.95868 (9)	0.0279 (2)
O6	0.54363 (7)	0.26725 (5)	1.18631 (10)	0.0285 (2)
C1	0.27523 (9)	0.11186 (6)	0.93025 (12)	0.0148 (2)
C2	0.18776 (9)	0.07855 (6)	0.68378 (12)	0.0160 (2)
C3	0.27744 (10)	0.03116 (7)	0.67123 (12)	0.0176 (2)
C4	0.37656 (10)	0.02098 (7)	0.80389 (13)	0.0196 (2)
C5	0.27947 (9)	0.15246 (6)	1.08134 (12)	0.0157 (2)
C6	0.18968 (10)	0.22037 (7)	1.05981 (14)	0.0215 (3)
H6A	0.1929	0.2448	1.1585	0.032*
H6B	0.1130	0.1973	1.0147	0.032*
H6C	0.2055	0.2626	0.9924	0.032*
C7	0.25766 (11)	0.08712 (7)	1.18957 (13)	0.0216 (3)
H7A	0.3156	0.0437	1.2026	0.032*
H7B	0.1810	0.0635	1.1472	0.032*
H7C	0.2624	0.1122	1.2882	0.032*
C8	0.08872 (9)	0.09093 (7)	0.54685 (12)	0.0171 (2)
C9	−0.07754 (10)	0.16603 (8)	0.43090 (14)	0.0259 (3)
H9A	−0.0423	0.1845	0.3526	0.039*
H9B	−0.1245	0.2103	0.4542	0.039*
H9C	−0.1262	0.1181	0.3938	0.039*
C10	0.44448 (10)	0.24266 (7)	1.08715 (13)	0.0185 (2)
C11	0.60365 (11)	0.33419 (8)	1.13972 (14)	0.0266 (3)
H11A	0.5518	0.3818	1.1074	0.032*
H11B	0.6333	0.3173	1.0541	0.032*
C12	0.70133 (10)	0.35578 (7)	1.27658 (13)	0.0206 (3)
C13	0.68387 (11)	0.36043 (8)	1.41951 (14)	0.0247 (3)
H13	0.6100	0.3491	1.4314	0.030*
C14	0.77345 (11)	0.38150 (8)	1.54519 (15)	0.0284 (3)
H14	0.7609	0.3838	1.6427	0.034*
C15	0.88144 (11)	0.39923 (8)	1.52900 (16)	0.0302 (3)
H15	0.9424	0.4144	1.6149	0.036*
C16	0.89961 (11)	0.39465 (8)	1.38730 (16)	0.0282 (3)
H16	0.9733	0.4067	1.3755	0.034*
C17	0.80992 (10)	0.37236 (7)	1.26174 (15)	0.0230 (3)
H17	0.8232	0.3685	1.1648	0.028*
H3	0.4221 (12)	0.1800 (8)	1.2505 (17)	0.024 (3)*
H2	0.4269 (13)	0.0577 (9)	1.0186 (18)	0.036 (4)*
H1	0.2178 (15)	0.0049 (10)	0.474 (2)	0.045 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0170 (5)	0.0159 (4)	0.0139 (4)	−0.0015 (3)	0.0029 (4)	−0.0008 (3)
N2	0.0177 (5)	0.0210 (5)	0.0134 (4)	0.0034 (4)	0.0014 (4)	−0.0024 (4)
N3	0.0182 (5)	0.0189 (5)	0.0116 (4)	−0.0021 (4)	0.0004 (4)	−0.0005 (4)
O1	0.0292 (5)	0.0293 (5)	0.0143 (4)	0.0056 (4)	0.0038 (4)	−0.0051 (3)
O2	0.0265 (5)	0.0372 (5)	0.0188 (4)	0.0140 (4)	0.0029 (4)	−0.0049 (4)
O3	0.0259 (5)	0.0283 (4)	0.0135 (4)	−0.0018 (3)	0.0012 (3)	−0.0026 (3)
O4	0.0173 (4)	0.0220 (4)	0.0158 (4)	0.0007 (3)	−0.0010 (3)	0.0012 (3)
O5	0.0294 (5)	0.0371 (5)	0.0142 (4)	−0.0095 (4)	0.0009 (3)	0.0056 (4)
O6	0.0273 (5)	0.0334 (5)	0.0189 (4)	−0.0152 (4)	−0.0031 (4)	0.0055 (4)
C1	0.0154 (5)	0.0143 (5)	0.0147 (5)	−0.0011 (4)	0.0040 (4)	0.0004 (4)
C2	0.0180 (6)	0.0156 (5)	0.0129 (5)	−0.0018 (4)	0.0019 (4)	0.0005 (4)
C3	0.0227 (6)	0.0164 (5)	0.0130 (5)	−0.0011 (4)	0.0037 (4)	−0.0015 (4)
C4	0.0220 (6)	0.0202 (6)	0.0158 (5)	0.0029 (4)	0.0040 (4)	−0.0011 (4)
C5	0.0158 (5)	0.0169 (5)	0.0135 (5)	−0.0011 (4)	0.0025 (4)	−0.0028 (4)
C6	0.0209 (6)	0.0212 (6)	0.0209 (6)	0.0033 (4)	0.0034 (5)	−0.0051 (5)
C7	0.0265 (6)	0.0216 (6)	0.0182 (6)	−0.0037 (4)	0.0087 (5)	−0.0015 (4)
C8	0.0183 (6)	0.0171 (5)	0.0149 (5)	−0.0043 (4)	0.0031 (4)	0.0009 (4)
C9	0.0209 (6)	0.0308 (7)	0.0201 (6)	0.0011 (5)	−0.0037 (5)	0.0048 (5)
C10	0.0197 (6)	0.0209 (5)	0.0139 (5)	−0.0017 (4)	0.0030 (4)	−0.0018 (4)
C11	0.0276 (7)	0.0319 (7)	0.0181 (6)	−0.0124 (5)	0.0028 (5)	0.0028 (5)
C12	0.0208 (6)	0.0190 (5)	0.0204 (6)	−0.0025 (4)	0.0034 (5)	0.0002 (4)
C13	0.0195 (6)	0.0305 (6)	0.0230 (6)	−0.0005 (5)	0.0041 (5)	−0.0011 (5)
C14	0.0306 (7)	0.0309 (7)	0.0206 (6)	0.0027 (5)	0.0020 (5)	−0.0040 (5)
C15	0.0239 (6)	0.0263 (6)	0.0317 (7)	−0.0014 (5)	−0.0067 (5)	0.0005 (5)
C16	0.0172 (6)	0.0249 (6)	0.0390 (7)	−0.0007 (5)	0.0019 (5)	0.0080 (6)
C17	0.0236 (6)	0.0202 (6)	0.0262 (6)	0.0016 (4)	0.0084 (5)	0.0042 (5)

Geometric parameters (Å, º) top

N1—C1	1.2937 (14)	C6—H6A	0.9800
N1—C2	1.3792 (14)	C6—H6B	0.9800
N2—C4	1.3692 (15)	C6—H6C	0.9800
N2—C1	1.3704 (14)	C7—H7A	0.9800
N2—H2	0.938 (16)	C7—H7B	0.9800
N3—C10	1.3446 (15)	C7—H7C	0.9800
N3—C5	1.4663 (14)	C9—H9A	0.9800
N3—H3	0.882 (15)	C9—H9B	0.9800
O1—C3	1.3456 (14)	C9—H9C	0.9800
O1—H1	0.918 (17)	C11—C12	1.5062 (16)
O2—C4	1.2308 (14)	C11—H11A	0.9900
O3—C8	1.2245 (14)	C11—H11B	0.9900
O4—C8	1.3230 (14)	C12—C17	1.3874 (18)
O4—C9	1.4491 (13)	C12—C13	1.3881 (18)
O5—C10	1.2154 (14)	C13—C14	1.3872 (17)
O6—C10	1.3489 (13)	C13—H13	0.9500
O6—C11	1.4413 (14)	C14—C15	1.389 (2)
C1—C5	1.5242 (15)	C14—H14	0.9500
C2—C3	1.3646 (16)	C15—C16	1.380 (2)
C2—C8	1.4881 (15)	C15—H15	0.9500
C3—C4	1.4602 (16)	C16—C17	1.3924 (18)
C5—C6	1.5259 (15)	C16—H16	0.9500
C5—C7	1.5291 (16)	C17—H17	0.9500

C1—N1—C2	116.87 (10)	H7A—C7—H7C	109.5
C4—N2—C1	123.91 (10)	H7B—C7—H7C	109.5
C4—N2—H2	117.4 (9)	O3—C8—O4	123.86 (10)
C1—N2—H2	118.4 (9)	O3—C8—C2	122.24 (11)
C10—N3—C5	123.00 (9)	O4—C8—C2	113.87 (9)
C10—N3—H3	115.1 (9)	O4—C9—H9A	109.5
C5—N3—H3	116.8 (9)	O4—C9—H9B	109.5
C3—O1—H1	104.1 (11)	H9A—C9—H9B	109.5
C8—O4—C9	115.30 (9)	O4—C9—H9C	109.5
C10—O6—C11	116.95 (9)	H9A—C9—H9C	109.5
N1—C1—N2	123.03 (10)	H9B—C9—H9C	109.5
N1—C1—C5	120.75 (10)	O5—C10—N3	126.23 (11)
N2—C1—C5	116.14 (9)	O5—C10—O6	124.12 (11)
C3—C2—N1	123.81 (10)	N3—C10—O6	109.62 (9)
C3—C2—C8	118.60 (10)	O6—C11—C12	105.89 (9)
N1—C2—C8	117.51 (10)	O6—C11—H11A	110.6
O1—C3—C2	126.16 (10)	C12—C11—H11A	110.6
O1—C3—C4	114.98 (10)	O6—C11—H11B	110.6
C2—C3—C4	118.86 (10)	C12—C11—H11B	110.6
O2—C4—N2	122.55 (10)	H11A—C11—H11B	108.7
O2—C4—C3	123.97 (11)	C17—C12—C13	118.85 (11)
N2—C4—C3	113.48 (10)	C17—C12—C11	120.61 (12)
N3—C5—C1	109.22 (9)	C13—C12—C11	120.53 (11)
N3—C5—C6	111.64 (9)	C14—C13—C12	120.51 (12)
C1—C5—C6	110.88 (9)	C14—C13—H13	119.7
N3—C5—C7	106.23 (9)	C12—C13—H13	119.7
C1—C5—C7	108.70 (9)	C13—C14—C15	120.27 (13)
C6—C5—C7	110.02 (10)	C13—C14—H14	119.9
C5—C6—H6A	109.5	C15—C14—H14	119.9
C5—C6—H6B	109.5	C16—C15—C14	119.59 (12)
H6A—C6—H6B	109.5	C16—C15—H15	120.2
C5—C6—H6C	109.5	C14—C15—H15	120.2
H6A—C6—H6C	109.5	C15—C16—C17	119.98 (12)
H6B—C6—H6C	109.5	C15—C16—H16	120.0
C5—C7—H7A	109.5	C17—C16—H16	120.0
C5—C7—H7B	109.5	C12—C17—C16	120.77 (13)
H7A—C7—H7B	109.5	C12—C17—H17	119.6
C5—C7—H7C	109.5	C16—C17—H17	119.6

C2—N1—C1—N2	−1.36 (16)	N1—C1—C5—C7	102.55 (12)
C2—N1—C1—C5	−178.04 (9)	N2—C1—C5—C7	−74.35 (12)
C4—N2—C1—N1	0.28 (18)	C9—O4—C8—O3	−5.78 (16)
C4—N2—C1—C5	177.10 (10)	C9—O4—C8—C2	171.97 (9)
C1—N1—C2—C3	0.47 (16)	C3—C2—C8—O3	4.06 (17)
C1—N1—C2—C8	−176.14 (10)	N1—C2—C8—O3	−179.15 (10)
N1—C2—C3—O1	−179.23 (10)	C3—C2—C8—O4	−173.74 (10)
C8—C2—C3—O1	−2.66 (18)	N1—C2—C8—O4	3.06 (14)
N1—C2—C3—C4	1.43 (17)	C5—N3—C10—O5	−11.21 (19)
C8—C2—C3—C4	178.00 (10)	C5—N3—C10—O6	170.86 (10)
C1—N2—C4—O2	−178.10 (11)	C11—O6—C10—O5	5.83 (18)
C1—N2—C4—C3	1.58 (16)	C11—O6—C10—N3	−176.18 (10)
O1—C3—C4—O2	−2.06 (18)	C10—O6—C11—C12	173.06 (10)
C2—C3—C4—O2	177.35 (11)	O6—C11—C12—C17	137.37 (11)
O1—C3—C4—N2	178.27 (10)	O6—C11—C12—C13	−43.44 (15)
C2—C3—C4—N2	−2.32 (16)	C17—C12—C13—C14	0.16 (18)
C10—N3—C5—C1	63.17 (13)	C11—C12—C13—C14	−179.05 (11)
C10—N3—C5—C6	−59.82 (14)	C12—C13—C14—C15	0.83 (19)
C10—N3—C5—C7	−179.76 (10)	C13—C14—C15—C16	−0.91 (19)
N1—C1—C5—N3	−141.95 (10)	C14—C15—C16—C17	0.00 (19)
N2—C1—C5—N3	41.15 (12)	C13—C12—C17—C16	−1.07 (17)
N1—C1—C5—C6	−18.51 (14)	C11—C12—C17—C16	178.14 (11)
N2—C1—C5—C6	164.59 (10)	C15—C16—C17—C12	1.00 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O5ⁱ	0.882 (15)	2.133 (15)	2.8911 (14)	143.7 (12)
N2—H2···O2ⁱⁱ	0.938 (16)	1.886 (16)	2.8135 (16)	169.3 (13)
O1—H1···O3	0.918 (17)	1.788 (17)	2.6163 (14)	148.7 (16)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₉N₃O₆
M_r	361.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	12.122 (2), 16.300 (3), 9.1766 (18)
β (°)	106.29 (3)
V (Å³)	1740.4 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.24 × 0.20 × 0.16

Data collection
Diffractometer	Bruker SMART diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.975, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	15564, 4142, 3386
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.103, 1.09
No. of reflections	4142
No. of parameters	250
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.24

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O5ⁱ	0.882 (15)	2.133 (15)	2.8911 (14)	143.7 (12)
N2—H2···O2ⁱⁱ	0.938 (16)	1.886 (16)	2.8135 (16)	169.3 (13)
O1—H1···O3	0.918 (17)	1.788 (17)	2.6163 (14)	148.7 (16)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, −y, −z+2.

Acknowledgements

The authors thank the funds of Hebei Province Science and Technology Research and Development Projects (No. 08276409D) and Hebei University of Science and Technology.

References

Bruker (1997). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Culbertson, T. P. (1979). J. Heterocycl. Chem. 16, 1423–1424. CrossRef CAS Google Scholar
Fun, H.-K., Balasubramani, K., Hazra, A., Kumar Das, M. & Goswami, S. (2009). Acta Cryst. E65, o1484–o1485. Web of Science CSD CrossRef IUCr Journals Google Scholar
Shang, Z.-H. & Shang, Q. (2007). Acta Cryst. E63, o2280–o2281. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Steigbigel, R. T., et al. (2008). N. Engl. J. Med. 359, 339–354. Web of Science CrossRef PubMed Google Scholar

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Volume 67| Part 6| June 2011| Page o1336

doi:10.1107/S1600536811016278

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Methyl 2-(2-{[(benz­yl­oxy)carbon­yl]amino}­propan-2-yl)-5-hy­dr­oxy-6-oxo-1,6-di­hydro­pyrimidine-4-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Methyl 2-(2-{[(benzyloxy)carbonyl]amino}propan-2-yl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate