4-(d-3-amino-3-carboxypropoxy) phenylglyoxylic acid oxime...

Details 4-(d-3-amino-3-carboxypropoxy) phenylglyoxylic acid oxime... 4-(d-3-amino-3-carboxypropoxy) phenylglyoxylic acid oxime...

C - Chemistry, Metallurgy

07

F

260/452, 260/468

C07F 7/18 (2006.01) C07D 307/33 (2006.01)

Patent

CA 1082727

ABSTRACT OF THE DISCLOSURE The present invention provides a novel process for preparing novel 4-(3-amino-3-carboxypropoxy)phenylglyoxylic acid oxime Amino-protected esters comprising cyclizing an alkylsulfonium iodide of an amino-protected methionine silyl ester to an amino-protected homoserine lactone; hydrolyzing the lactone to an amino-protected homoserine in aqueous base; coupling an ester of the amino-protected homoserine with an ester of 4-hydroxyphenylglyoxylic acid or a pro- tected-oxime thereof to form an ether; and if desired forming the oxime of the ether. The present process is stereospecific and provides a product having the same isomeric configuration as the starting material. The D- isomer is preferred. The product is useful in preparing the antibiotic FR 1923.

288251

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