(4S)-Benzyl 4-isopropyl-5-oxo-1,3-oxazolidine-3-carboxyl­ate

Jian-Bin Wu; Kan Lin; Jian-Nan Guo; Guo Tang; Yu-Fen Zhao

doi:10.1107/S1600536808004455

. 2008 Mar 12;64(Pt 4):o685. doi: 10.1107/S1600536808004455

(4S)-Benzyl 4-isopropyl-5-oxo-1,3-oxazolidine-3-carboxylate

Jian-Bin Wu ^a, Kan Lin ^a, Jian-Nan Guo ^a,^*, Guo Tang ^a, Yu-Fen Zhao ^a

PMCID: PMC2961013 PMID: 21202077

Abstract

In the crystal structure of the title compound, C₁₄H₁₇NO₄, obtained by the reaction of N-benzoxycarbonyl-l-valine, paraformaldehyde and 4-methylbenzenesulfonic acid, molecules are linked by C—H⋯O hydrogen bonds, generating linear chains parallel to the a axis. C—H⋯π interactions of stacked benzene rings also provide stability for the crystal structure.

Related literature

For related literature, see: Dorow & Gingrich (1999 ▶); Allen et al. (1987 ▶); Pavel et al. (1993 ▶); Reddy et al. (2000 ▶).

Experimental

Crystal data

C₁₄H₁₇NO₄
M _r = 263.29
Orthorhombic,
a = 6.0528 (2) Å
b = 13.1581 (5) Å
c = 16.6778 (6) Å
V = 1328.28 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 153 (2) K
0.50 × 0.17 × 0.09 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.953, T _max = 0.991
5718 measured reflections
1368 independent reflections
1100 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.028
wR(F ²) = 0.062
S = 0.99
1368 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808004455/cf2183sup1.cif

e-64-0o685-sup1.cif^{(18.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808004455/cf2183Isup2.hkl

e-64-0o685-Isup2.hkl^{(67.6KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg is the centroid of the C9–C14 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O5ⁱ	0.97	2.32	3.258 (2)	163
C12—H12A⋯Cgⁱⁱ	0.93	3.37	3.963 (3)	124

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors acknowledge financial support from the Key Foundation of Science and Technology Project of Fujian Province, China (Key grant No. 2002H011).

supplementary crystallographic information

Comment

The title compound (I) belongs to a class of 5-oxazolidinone and has been used to synthesize dipeptides and a series of biologically active molecules (Dorow & Gingrich, 1999).

In the compound, the oxazolidine ring is formed by the reaction of N-benzoxycarbonyl-L-valine, paraformaldehyde, and 4-methylbenzenesulfonic acid. The phenyl and the oxazolidine rings make a dihedral angle of 49.7 (1) (Fig. 1). The absolute configuration (S) of the stereocentre C4 remains unchanged during the synthetic procedure. An X-ray crystal structure determination of the molecular structure of compound (I) was carried out to determine its conformation. The bond lengths are within normal ranges (Allen et al., 1987).

The packing is shown in Fig. 2. The occurrence of C—H···O hydrogen bond interactions lead to the formation of linear chains parallel to the a axis. The packing is further stabilized by C—H···π interactions of stacked benzene rings in the chains (Fig. 3), with typical geometry (Pavel et al., 1993).

Experimental

The title compound was prepared by a method based on one described by Reddy et al. (2000). A mixture of N-benzoxycarbonyl-L-valine (7.53 g, 3 mmol), paraformaldehyde (1.8 g, 6 mmol) and 4-methylbenzenesulfonic acid (PTSA, 0.31 g, 1.8 mmol) in benzene (25 ml) was refluxed, using a Dean–Stark apparatus, for about 1 h. After cooling, the resulting mixture was washed with 0.3 M aqueous K₂CO₃ solution (30 ml) followed by saturated aqueous NaCl solution (30 ml). The organic layer was separated and dried with Mg₂SO₄, filtered and concentrated in vacuo to give the crude product as a white solid (5.12 g, 65%). Crystals suitable for X-ray diffraction were obtained from an ethanol solution.