Crystal structure of N-tosyl-2-methylserine-β-lactone, C11H13NO4S

Carolin Lauf, Clemens Bruhn, Herbert Frauenrath
2010 Zeitschrift für Kristallographie - New Crystal Structures  
C 11 H 13 NO 4 S, orthorhombic, P2 1 2 1 2 1 (no. 19), a =5.7011(4) Å, b =8.9203(6) Å, c =23.571(2) Å, Source of material The preparation was carried out under nitrogen atmosphere at -10 .°Cb ya dding 3.3 mmol (0.57 g) diethyl azodicarboxylate (DEAD) to asolution of 3.3 mmol (0.866 g) triphenylphosphine in 6mldry ethyl acetate [1]. After stirring for 15 min the betaine complex [3] was formed (monitored by GC). Then 3m mol (0.816 .g) N-tosyl-2-methylserine was added, the reaction mixture was
more » ... ion mixture was stirred for 1hat-10°Cand for further 2hatroom temperature. After dilution with 6m ln -hexane it was stored for 2ha t -20 .°C . The precipitate of N,N'-diethoxycarbonylhydrazine and triphenylphosphine oxide was filtered off. The solvent was removed in vacuo and the oily residue was purified by column chromatography using ethyl acetate/n-hexane (1:1) as eluent (yield 30.-40%). Crystals of the title compound precipitated over aperiod of 3d ays from ah ighly concentrated solution in dichloromethane covered with paraffine oil of low viscosity.
doi:10.1524/ncrs.2010.0058 fatcat:jp5zdxwpwzhirnvxejdhkfiiru