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Synthesis of disodium D (-)-6-(2-phenyl-2-sulfoacetamido-1-14C) penicillanate (sulfocillln-14C) and 6-(2-isobutyl-β,γ-3H2-sulfo-2-phenylacetamido-1-14C) penicillanic acid (SP-421-3H, 14C)

✍ Scribed by Nobuyoshi Haayshi; Shinji Kato; Tadashi Toga; Koji Nishijima; Tadashi Hanaoka; Hiroshi Akimoto; Keiichi Sugimoto

Publisher
John Wiley and Sons
Year
1975
Tongue
French
Weight
305 KB
Volume
11
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

The syntheses of disodium 6‐(2‐phenyl‐2‐sulfoacetamido‐1‐^14^C) peniaillanate (IV) and 6‐(2‐isobutyl‐β,γ‐ ^3^H~2~‐sulfo‐2‐phenyl‐acetamido‐1‐^14^C) penicillanic acid (XII) are described. The optically active D(‐)‐IV was obtained by the fractional crystallization of diastereoisomeric mixture which was prepared from phenylacetia acid‐1‐^14^C (I). The compound double labelled with ^3^H and ^14^C, XII, was synthesized by the reaction of trimethylsilyl 6‐aminopenicillanate with 2‐isobutyl‐β,γ‐^3^H~2~‐ sulfo‐2‐phenylacetyl chloride‐1‐^14^C (XI) which was prepared from isobutanol‐2,3‐^3^H~2~ and I. The overall radiochemical yields of XII, at the specific activities of 9 mCi (^3^H)/mmole and 2 mCi (^14^C)/mmole, were 34% yield based on isobutanol‐2,3‐^3^H~2~ and 17% yield based on I respeatively.

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