Process for preparing ACHPA

Details Process for preparing ACHPA Process for preparing ACHPA

1987-07-31

1988-11-29

Shippen, Michael L.

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

Organic compounds

Carboxylic acid esters

C07C125065

Patent

active

047883227

ABSTRACT:
Process comprising coupling of an acylimidazole-activated derivative of a reduced and protected phenylalanine with the magnesium salt of malonic acid monoethyl ester to produce the beta-ketoester, which is subsequently reduced with NaCNBH.sub.3 /THF in glacial acetic acid to afford a separable mixture of 3-S and 3-R 3-hydroxy-(4S)-4-(N-.alpha.-BOC)amino-5-cyclohexylpentanoic acid, such that large-scale, high yield production of optically-active ACHPA is significantly improved.

REFERENCES:
patent: 3969406 (1976-07-01), Tenud
patent: 4021480 (1977-05-01), Tenud
patent: 4296242 (1981-10-01), Tattanahalli
patent: 4487963 (1984-12-01), Bock
patent: 4681972 (1987-07-01), Kaltenbronn
Borch, J. Am. Chem. Soc., 93, pp. 2897-2904 (1971).
Boger, J. Med. Chem., 28, pp. 1779-1790 (1985).

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