Process for preparing .alpha.-aspartyl-L-phenylalanine methyl es

Details Process for preparing .alpha.-aspartyl-L-phenylalanine methyl es Process for preparing .alpha.-aspartyl-L-phenylalanine methyl es

1984-05-10

1987-01-20

Phillips, Delbert R.

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

Organic compounds

Carboxylic acid esters

26099821, 530801, C07C10132, C07K 506

Patent

active

046380817

ABSTRACT:
A process for preparing .alpha.-L-aspartyl-L-phenylalanine methyl ester consisting of:
bringing N-formyl-L-aspartic anhydride and L-phenylalanine methyl ester, in a molar ratio equal or approximately equal to 1:1, into contact with a solid cation exchange resin having free sulphonic, phosphonic or carboxylic acid groups, the ration of the acid equivalents of said resin acid groups to the number of moles of the one or other reagent being equal to or less than about 1:1, and operating in the liquid phase in an inert organic solvent at a temperature of about 40.degree. C. or less, until a mixture of N-formyl-.alpha.-L-aspartyl-L-phenylalanine methyl ester and N-formyl-.beta.-L-aspartyl-L-phenylalanine methyl ester forms in which the .alpha. isomer prevails over the .beta. isomer;
deformylating said N-formyl-.alpha.-L-aspartyl-L-phenylalanine methyl ester and N-formyl-.beta.-L-aspartyl-L-phenylalanine methyl ester; and
separating and recovering the .alpha.-L-aspartyl-L-phenylalanine methyl ester from said deformylated products.

REFERENCES:
patent: 3786039 (1974-01-01), Ariyoski et al.
patent: 4309341 (1982-01-01), Kubo et al.
patent: 4543349 (1985-09-01), Callahan et al.
Derwent Abst., 87762x/47, Mar. 28, 1975, J5 1113-841.
Yasutake et al, Bull. Chem. Soc. Jpn. 50 (9), 2413-2416 (1977).
Pavlova, Russian Chem. Rev. 50 (4), 316-323 (1981).
Chemical Abstracts, Yasutake et al., 88:23368g, referring to Bull. Chem. Soc. Jpn. 50(9), 2413-2416(1977).

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