Method for producing .alpha.-hydroxy-.beta.-aminocarboxylic acid

Details Method for producing .alpha.-hydroxy-.beta.-aminocarboxylic acid Method for producing .alpha.-hydroxy-.beta.-aminocarboxylic acid

1998-06-17

1999-03-16

Ambrose, Michael G.

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

Organic compounds

Carboxylic acid esters

548479, 560253, 564391, C07C32343, C07C32341, C07C32325

Patent

active

058832840

ABSTRACT:
The present invention provides a simple and inexpensive method for producing .alpha.-hydroxy-.beta.-aminocarboxylic acids and their esters.
An ester of an N-protected .alpha.-amino acid ester is converted into a .beta.-ketosulfoxide, which is then processed with an acid to give an .alpha.-ketohemimercaptal. Next, this is acylated and then processed with a base to obtain an N-protected .alpha.-acyloxy-.beta.-amino-thioester, which is then saponified to obtain an intended compound. According to the method of the present invention, it is possible to produce .alpha.-hydroxy-.beta.-aminocarboxylic acid derivatives, which are intermediates in producing various HIV protease inhibitors, renin inhibitors and carcinostatics, from a-amino acids. The method comprises reduced reaction steps, the selectivity in the method to give the intended product is high, and the yield of the product obtained is high.

REFERENCES:
Database Caplus on STN, Chemical Abstracts Service (Columbus, Ohio), Accession No. 1976:58996, Tsuchihashi, G. et al., JP 50-117717, abstract.
Database Caplus on STN, Chemical Abstracts Service (Columbus, Ohio), Accession No. 1975:125014, Tsuchihashi, G. et al., J. Am. Chem. Soc., 1975, 97(3), 596-9, abstract.
Pusino, A. et al., Gazzetta Chimica Italiana, 1984, 114, 395-8.

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