Organic compounds -- part of the class 532-570 series – Organic compounds – Esters having the thiocarboxylate group – -cx- – wherein the...
Patent
1996-10-04
1998-01-06
Ambrose, Michael G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Esters having the thiocarboxylate group, -cx-, wherein the...
558254, C07C32722
Patent
active
057056714
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:
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Honda Yutaka
Izawa Kunisuke
Suzuki Takayuki
Ajinomoto Co. Inc.
Ambrose Michael G.
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