Process for producing .alpha.-L-aspartyl-L-phenylalanine methyl

Details Process for producing .alpha.-L-aspartyl-L-phenylalanine methyl Process for producing .alpha.-L-aspartyl-L-phenylalanine methyl

1983-04-13

1987-08-04

Brown, Johnnie R.

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

Organic compounds

Carboxylic acid esters

560 40, C07C10132

Patent

active

046847456

ABSTRACT:
A process for producing .alpha.-L-aspartyl-L-phenylalanine methyl ester or its hydrochloride which comprises contacting N-formyl-.alpha.-L-aspartyl-L-phenylalanine methyl ester with a mixture of methanol and a highly concentrated hydrochloric acid at a temperature of between 0.degree. and 40.degree. C., whereby the amino-protecting formyl group is removed and .alpha.-L-aspartyl-L-phenylalanine methyl ester crystalizes, and isolating the hydrochloride crystals, and, if desired, converting the hydrochloride to free .alpha.-L-aspartyl-L-phenylalanine methyl ester, is disclosed along with variations thereof. The process is commerically advantageous in that it utilizes inexpensive materials while minimizing hydrolysis of the peptide bond.

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Sheehan et al., J. Am. Chem. Soc., 80, 1158 (1958).
Vigneaud et al., J. Biol. Chem., 98, 577 (1932).

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