Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof
Patent
1992-08-17
1994-06-28
Shippen, Michael L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acids and salts thereof
560114, 560185, 560233, 562401, 562579, 562581, C07C 5908
Patent
active
053248562
ABSTRACT:
Disclosed is a process for making an .alpha.-hydroxy acid which is essentially all L or all D with respect to the chiral C atom bonded to the carboxy group of said acid which comprises (1) hydrocarboxylating an enol acylate, which has a chiral C atom that is essentially all L or all D, with CO and water or an organic hydroxyl compound, thereby producing a reaction mixture containing diastereomeric .alpha.-acyloxy acids or esters having two chiral centers and having essentially no enantiomeric pairs, (2) separating the diastereomers by conventional physical means and (3) hydrolyzing at least one of said separated diastereomers to make at least the .alpha.-hydroxy acid which is essentially all L or all D with respect to the chiral C atom bonded to the carboxy group of said acid.
Also disclosed is a process for making an .alpha.-hydroxy acid which is essentially all L or all D with respect to the chiral C atom bonded to the carboxy group of said acid which comprises (1) hydrocarboxylating an enol acylate, the enol portion of which has a chiral C atom that is essentially all L or all D, with CO and water or an organic hydroxyl compound, thereby producing a reaction mixture containing diastereomeric .alpha.-acyloxy acids or esters having two chiral centers and having essentially no enantiomeric pairs, (2) hydrolyzing the product of (1) to make a diastereomeric mixture containing .alpha.-hydroxy acids, and (3) separating by conventional physical means from the product of (2) at least one .alpha.-hydroxy acid which is essentially all L or all D with respect to the chiral C atom bonded to the carboxy group of said acid.
REFERENCES:
patent: 4377708 (1983-03-01), Morris
Migrdichian, "Organic Synthesis," vol. 1, p. 205 (1957).
March, "Advanced Organic Chemistry, Reactions, Mechanisms and Structure," pp. 92-94 (1969).
March, "Advanced Organic Chemistry, Reactions, Mechanisms and Structure," 2nd Ed., pp. 736-737 (1977).
Roberts, "Basic Principles of Organic Chemistry," pp. 597-603 (1964).
Burrington James D.
Cesa Mark C.
Dubbert Robert A.
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