Diisopropyl [(benzoyl­amino)­(phen­yl)meth­yl]phospho­nate

Hua Fang; Mei-Juan Fang; Ying Xu; Wen-Cheng Yu; Yu-Fen Zhao

doi:10.1107/S1600536809006382

. 2009 Feb 28;65(Pt 3):o642. doi: 10.1107/S1600536809006382

Diisopropyl [(benzoylamino)(phenyl)methyl]phosphonate

Hua Fang ^a,^*, Mei-Juan Fang ^b, Ying Xu ^b, Wen-Cheng Yu ^b, Yu-Fen Zhao ^c

PMCID: PMC2968692 PMID: 21582291

Abstract

The title compound, C₂₀H₂₆NO₄P, has been obtained by the reaction of benzoyl chloride and diisopropyl[amino(phenyl)methyl]phosphonate. The dihedral angle between the planes of the benzoylamino group and the phenyl ring is 77.0 (2)°. The crystal structure is stabilized by strong intermolecular N—H⋯O hydrogen bonds between the doubly bonded phosphoryl O atom and the amide N atom which link the molecules into pairs about a center of symmetry.

Related literature

For the biological activity and pharmaceutical interest of α-hydroxyphosphonic acid esters, see: Stowasser et al. (1992 ▶); Chen et al. (1995 ▶). For their use as reagents in the synthesis of enol ethers and α-ketophosphonates, see: Babak & Rahman (2001 ▶). For the synthesis, see: Drescher et al. (1995 ▶). For bond lengths and angles in related compunds, see: Smaardijk et al. (1985 ▶). graphic file with name e-65-0o642-scheme1.jpg

Experimental

Crystal data

C₂₀H₂₆NO₄P
M _r = 375.39
Triclinic,
a = 10.839 (4) Å
b = 10.925 (5) Å
c = 11.057 (5) Å
α = 61.364 (8)°
β = 83.362 (8)°
γ = 60.470 (6)°
V = 987.3 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 273 K
0.28 × 0.21 × 0.05 mm

Data collection

Bruker SMART APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.956, T _max = 0.992
4991 measured reflections
3411 independent reflections
2509 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.065
wR(F ²) = 0.174
S = 0.98
3411 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.44 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809006382/fl2235sup1.cif

e-65-0o642-sup1.cif^{(21.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006382/fl2235Isup2.hkl

e-65-0o642-Isup2.hkl^{(167.3KB, hkl)}

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2ⁱ	0.86	2.05	2.895 (3)	165

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the National Natural Science Foundation of China (No. 40806032) and the Scientific Research Foundation of the Third Institute of Oceanography, SOA (No. 2009005).

supplementary crystallographic information

Comment

In recent years α-hydroxyphosphonic acids esters have attracted much attention due to their wide biological activity (Stowasser et al., 1992) and pharmaceutical interest (Chen et al., 1995). They are useful reagents for the synthesis of enol ethers and α-ketophosphonates (Babak et al., 2001). Bond lengths and angles in the title compound, (I), are in agreement with the values reported for related compounds (Smaardijk et al., 1985). The dihedral angle between the planes of the benzoylamino group and phenyl ring is 103.0 (2)° (Fig. 1). The amide N atom is involved in a hydrogen-bonding interaction with the phosphoryl O atom of a neighboring molecule linking the molecules into pairs around a centerof symmetry (Table 1 and Fig. 2).

Experimental

A solution of dry dichloromethane (20 ml) containing (amino-phenyl-methyl)-phosphonic acid diisopropyl ester (1 mmol, 0.27 g) and triethylamine (0.4 ml) was added dropwise to a solution of dichloromethane (10 ml) containing benzoyl chloride (1.2 mmol, 0.17 g). The reaction mixture was stirred for 6 h at room temperature and the solvent was then removed under reduced pressure to give a residue, which was extracted with ethyl acetate (3 × 15 ml). The solution was dried over anhydrous MgSO₄ and concentrated under vacuum to obtain a slurry residue, which was purified by silica gel column chromatography (petroleum ether/ethyl acetate = 2:1) to give (I) as a colorless amorphous solid (Drescher, et al., 1995). Single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of a petroleum ether /dichloromethane solution (1:1 v/v).