Ethyl [1S, 2RS]-and [1S,2S]-2-[2-chloro-propanoyloxy]propanoate. Preparation and hydrolysis

Ethyl (1S,2RS)-2-(2-chloropropanoyloxy)propanoate ((1S,2RS)-(I)) was obtained from rac-2-chloropropionyl chloride and ethyl L-lactate. (1S,2S)- (I) was also synthesized from (S)-2-chloropropionyl chloride and ethyl L-lactate with 93% d.e. (I) was undertaken hydrolysis by different media: NaOH/THF-H2O, Na2CO3/THF-H2O, LiOHxH2O/THF-H2O, 25% NaOH/H2O, and weakly acidic ion-exchange resin Amberlite IRC748 dispersion in MeOH. (1S,2RS)-2-(2-Chloropropanoyloxy) propanoic acid (II) diastereomers were identified as products of acidic hydrolysis with the ionic resin. GC/MS, HPLC and HPLC/MS analyses of resulted products are presented