Patent ID: 6278002
Filing Date: 2001-08-21
Classification: C07D

Abstract:
A process for producing (2R,3S)-3-amino-4-phenylbutane-1,2-epoxide compounds represented by the general formula (8): ##STR6##wherein R.sub.1 represents an amino-protecting group,which comprisestreating a (2S,3S)-3-amino-1-halo-2-hydroxy-4-phenylbutane compound represented by the general formula (1) or a (2S,3S)-3-amino-4-phenylbutane-1,2-epoxide represented by the general formula (2): ##STR7##wherein R.sub.1 is as defined above and X represents a halogen atom, ##STR8##wherein R.sub.1 is as defined above,with a carboxylic acid quaternary ammonium salt represented by the general formula (3) or a carboxylic acid metal salt represented by the general formula (4):R.sub.3 R.sub.4 R.sub.5 R.sub.6 N.sup.+ OCOR.sub.2.sup.- (3)wherein R.sub.2 represents an alkyl, aryl or aralkyl group and R.sub.3, R.sub.4, R.sub.5 and R.sub.6 may be the same or different and each independently represents an alkyl or aralkyl group,R.sub.2 COO.sup.- M.sup.+ (4)wherein R.sub.2 is as defined above and M represents a metal atom, and a quaternary ammonium salt represented by the general formula (5):R.sub.3 R.sub.4 R.sub.5 R.sub.6 N.sup.+ Y.sup.- (5)wherein R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are as defined above and Y represents a halogen atom,to give a (2S,3S)-1-acyloxy-3-amino-2-hydroxy-4-phenylbutane compound represented by the general formula (6): ##STR9##wherein R.sub.1 and R.sub.2 are as defined above,further treating said (2S,3S)-1-acyloxy-3-amino-2-hydroxy-4-phenylbutane compound with a sulfonic acid halide in the presence of an organic base,to give a (2S,3S)-1-acyloxy-3-amino-2-sulfonyloxy-4-phenylbutane compound represented by the general formula (7): ##STR10##wherein R.sub.1 and R.sub.2 are as defined above and R.sub.7 represents an alkyl, aryl or aralkyl group,furthermore treating said (2S,3S)-1-acyloxy-3-amino-2-sulfonyloxy-4-phenylbutane compound with an inorganic base.