Preparation of N-protected .alpha.-L-aspartyl-L-phenylalanine me

Details Preparation of N-protected .alpha.-L-aspartyl-L-phenylalanine me Preparation of N-protected .alpha.-L-aspartyl-L-phenylalanine me

1992-01-21

1994-04-12

Dees, Jose G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

560 41, 560 38, C07C22900

Patent

active

053027434

ABSTRACT:
Disclosed is an improved process for the preparation of an N-protected .alpha.-L-aspartyl-L-phenylalanine methyl ester from an N-protected L-aspartic anhydride and L-phenylalanine methyl ester, the improvement which comprises employing the L-phenylalanine methyl ester in the form of a mineral acid salt thereof and conducting the reaction either (a) in an organic solvent and in the presence of a salt of an organic carboxylic acid, or (b) in an organic solvent comprising an organic carboxylic acid and in the presence of at least one member of the group consisting of an alkali metal or an alkaline earth metal inorganic base, an ammonium alkali metal or alkaline earth metal salt of an organic carboxylic acid and ammonium carbonate. The starting N-protected aspartic anhydride, e.g., N-benzyloxycarbonyl-L-aspartic anhydride, can be produced by the reaction of N-protected aspartic acid with phosgene. When the N-protecting group sibenzyloxycarbonyl and the solvent is acetic acid, the desired product can be isolated from the reaction mixture in crystalline form in high purity by adding water thereto.

REFERENCES:
patent: 3872110 (1975-03-01), Ariyoshi et al.
patent: 4680403 (1987-07-01), Hisamitsu et al.

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