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Synthesis of 1‐ethyl‐1‐(2‐hydroxyethyl)aziridinium‐1,2‐ 14 C 2 chloride ( 1 ) ([ 14 C]AF64A)
Author(s) -
Mistry Jehangir S.,
Abraham Donald J.,
Hanin Israel
Publication year - 1989
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580271002
Subject(s) - chemistry , yield (engineering) , ethyl chloride , chloride , diethylamine , ethylene , medicinal chemistry , derivative (finance) , ethylene oxide , hydrochloride , ethanol , nuclear chemistry , organic chemistry , catalysis , materials science , polymer , copolymer , economics , financial economics , metallurgy
1‐Ethyl‐1‐(2‐hydroxyethyl)aziridinium‐1,2‐ 14 C 2 chloride ( 1 ) ([( 14 C]AF64A), the labelled analogue of a selective presynaptic cholinotoxin, was prepared from labelled ethylene oxide. The synthetic intermediate, 1,2‐ 14 C 2 ‐2[ethyl[2‐[(tetrahydro‐2 H ‐pyran‐2‐yl)oxy]ethyl]amino]ethanol, obtained in good yield by the reaction of 2‐[(tetrahydro‐2 H ‐pyran‐2‐yl)oxy]diethylamine with [ 14 C] ethylene oxide, was converted to the corresponding ethyl chloride derivative using CH 3 SO 2 Cl/n‐BuLi. Subsequent removal of the THP group under mild acidic condition gave the mono‐armed mustard as a stable hydrochloride salt in an overall chemical yield of 46% and radiochemical yield of 27%. Conversion of the mustard compound to the corresponding aziridinium species was followed by 1 H NMR.