Process for 4-(D-3-amino-3-carboxypropoxy)-phenylglyoxylic acid

Details Process for 4-(D-3-amino-3-carboxypropoxy)-phenylglyoxylic acid Process for 4-(D-3-amino-3-carboxypropoxy)-phenylglyoxylic acid

1977-08-17

1982-10-19

Breitenstein, G. T.

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

Organic compounds

Carboxylic acid esters

260239A, C07C125065, C07C125067

Patent

active

043551726

ABSTRACT:
Process for 4-(D-3-amino-3-carboxypropoxy)phenylglyoxylic acid oxime as an amino-protected ester comprising alkylating an amino-protected D-methionine silyl ester with an alkyl or benzyl iodide; cyclizing the alkylsulfonium iodide to an amino-protected D-homoserine lactone; hydrolyzing the lactone to an amino-protected D-homoserine in aqueous base; coupling, to form an ether, the amino-protected D-homoserine as an ester with an ester of 4-hydroxyphenylglyoxylic acid; and forming the oxime of the ether or alternatively coupling the D-homoserine ester with a protected-oxime of an esterified 4-hydroxyphenylglyoxylic acid. The product is useful in preparing the antibiotic FR 1923.

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patent: 3923977 (1975-12-01), Aoki et al.
patent: 4237305 (1980-12-01), Kamiya et al.
Lawson et al., J.A.C.S., 83, 1509 (1961).
Morrison & Boyd, "Organic Chem.", Allyn & Bacon, Inc., Boston, Mass., 3rd Ed., p. 674 (1973).
Lawson et al., J.A.C.S., 84, 1715-1718 (1962).
Mashimoto et al., J.A.C.S., 98(10), 3023-3025, 1976.
Wagner & Zook, Synthetic Organic Chem., John Wiley & Sons, Inc., pp. 565-573 & 585-589 (1965).
McOmie, Protective Groups in Organic Chem., Plenum Press, pp. 58, 59, 86, 87, 185-187, 210-211 (1973).
Bittner et al., Chem. Ind., (London) p. 281 (1975).

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