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Synthesis of disodium D (‐)‐6‐(2‐phenyl‐2‐sulfoacetamido‐1‐ 14 C) penicillanate (sulfocillln‐ 14 C) and 6‐(2‐isobutyl‐β,γ‐ 3 H 2 ‐sulfo‐2‐phenylacetamido‐1‐ 14 C) penicillanic acid (SP‐421‐ 3 H, 14 C)
Author(s) -
Haayshi Nobuyoshi,
Kato Shinji,
Toga Tadashi,
Nishijima Koji,
Hanaoka Tadashi,
Akimoto Hiroshi,
Sugimoto Keiichi
Publication year - 1975
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590110312
Subject(s) - yield (engineering) , chemistry , isobutanol , trimethylsilyl , nuclear chemistry , fractional crystallization (geology) , crystallization , medicinal chemistry , chloride , stereochemistry , organic chemistry , alcohol , materials science , geochemistry , basalt , metallurgy , geology
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.