Interphenylene 11,12-secoprostaglandins

Details Interphenylene 11,12-secoprostaglandins Interphenylene 11,12-secoprostaglandins

1978-12-13

1979-11-20

Killos, Paul J.

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

Organic compounds

Carboxylic acid esters

560 61, 560 62, 260559H, 260559B, 562472, 562471, 562465, C07C17700

Patent

active

041752031

ABSTRACT:
Novel interphenylene derivatives of 11,12-secoprostaglandins are prepared by the stepwise alkylation of the ethyl ester or the t-butyl ester of acetoacetic acid. One such method involves treatment of the t-butyl ester of acetoacetic acid with a strong base to form the anion followed by treatment with ethyl p-(3-bromopropyl)benzoate to produce ethyl 4-(4-tert-butoxycarbonyl-5-oxo-hexyl)benzoate, subsequently reacting the anion of the thus-formed benzoate with 1-chloro-4-acetoxynonane to produce ethyl 4-(4-acetyl-4-tert-butoxycarbonyl-8-acetoxytridecyl)benzoate followed by decarboxylation and alkaline hydrolysis to produce the desired product 4-(4-acetyl-8-hydroxytridecyl)benzoic acid which is useful as a pharmaceutical in the treatment of patients with renal failure and in the prevention of transplant rejection.

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