Emeriamine dihydrochloride

N-chloro-N-sodium carbamates are more nucleophilic than neutral amides and hence it was proposed that they can facilitate the ring opening of aziridine derivativesThe synthesis of the title compounds was carried out by a reaction of N-(nosyl)aziridines with N-chlorocarbamate 1,1-dimethylethyl ester sodium salt, whereby the nosyl group may be easily removed for further transformation.This method was applied to the transformation of D-aspartic acid into (2R)-2-amino-3-carboxy-N,N,N-trimethyl-1-propanaminium inner salt (emeriamine).The synthesis of the target compound was achieved by a ring opening of an aziridine derivative (I) with tert-Bu chlorocarbamate sodium salt and the product thus formed was a chiral diamine derivative (II).II was transformed into the target compound emeriamine [i.e., (2R)-2-amino-3-carboxy-N,N,N-trimethyl-1-propanaminium inner salt] (III).