Crystal structure of N-(diphenyl)methyl-N-(3′,3′-dimethyl-2′-oxo)butyl- 2(R),3(R)-epoxybutyramide, C23H27NO3

B. Tinant, M. Laurent, J. Marchand-Brynaert
2006 Zeitschrift für Kristallographie - New Crystal Structures  
C 23H27NO3, monoclinic, P1211 (no. 4), a = 8.669(3) Å, b = 22.880(5) Å, c = 10.220(3) Å, b = 96.04(2)°, V = 2015.9 Å 3 , Z = 4, R gt(F) = 0.039, wRref(F 2 ) = 0.106, T = 125 K. Source of material The title compound was prepared from sodium 2(R),3(R)-epoxybutyrate (mixed salt with NaBr) [1] and 1-(diphenylmethyl)amino-3,3-dimethyl-2-butanone [2] in a one-pot process. Epoxybutyrate was first activated with oxalylchloride in THF at 5°C, then pyridine and the amino-ketone were added and reacted for
more » ... ded and reacted for 2 h at 20°C. After work-up and column chromatography on silicagel, the epoxybutyramide was recovered in 73 % yield (R F = 0.33; CH 2Cl2/EtOH, v/v 10:1). Crystallization from CH2Cl2/MeOH/ H 2O (1:1:1) gave white crystals suitable for X-ray diffraction analysis (m.p. = 157-158°C, [a] 20 = +10.8 (c = 1.03, CHCl3), mass (EI) m/e = 365.2 [2]).
doi:10.1524/ncrs.2006.221.1.68 fatcat:fkqlrpfodrb7bk4xqvysqc7oyy