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Synthesis of 3-cyano-4-methyl-5(14C)-methyl-2-(5-14C)pyrrolyloxamic acid

✍ Scribed by I. L. Honigberg; N. M. Meltzer; C. D. Blanton Jr.

Publisher
John Wiley and Sons
Year
1979
Tongue
French
Weight
181 KB
Volume
16
Category
Article
ISSN
0022-2135

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✦ Synopsis

A synthesis of 3-cyano-4-methyl-5 ( 14 C)-methyl-2-(5-14C)pyrrolyloxamic acid is described. The compound, having specific activity of 66.7 pCi/mmole, was obtained in 19.68% overall yield from uniformly labelled 14C-l-alanine. 14 14 Key Words: 3-Cyano-4-methyl-5( C)-methyl-2-(5-C)pyrrolyloxamic acid, heterocyclic oxamic acid, antiallergy activity.

INTRODUCT I >

The title compound is one of a group of heterocyclic oxamates (1) which were screened for biological activity and found to possess antiallergy activity ( 2 ) . The active form was shown to be the free acid (3). Investigations of the metabolic fate and mechanism by which this compound prevents mediator release from the mast cell required the synthesis of the I4C-labeled compound, which has not been previously reported.

Discussion

Ethyl (3-cyano-4,5-dimethyl-2-pyrrolyl)oxamate 4 was first prepared as one of a series of heterocyclic oxamates synthesized as possible indole isostere precursors. In the synthesis of the title compound no intermediates were isolated, and only the final product was recrystallized. A convenient synthesis of the oxamate, as reported by Blanton, gal. (l), begins with the preparation of the amino-ketone 2 by the method of Wiley and Borum (4) and the aminesubstituted pyrrole 2 by the method of Gewald (5).

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