Interphenylene 11,12-secoprostaglandins

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

1976-12-17

1979-04-17

Killos, Paul J.

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

Organic compounds

Carboxylic acid esters

560 55, 560254, 562463, 562465, C07C 6976

Patent

active

041502353

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 pharmaceutical in the treatment of patients with renal failure and in the prevention of transplant rejection.

REFERENCES:
patent: 3379752 (1968-04-01), Bolhofer
patent: 3956374 (1976-05-01), Shepard

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