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Synthesis of 3‐hydroxy‐N,N‐dimethyl‐cis‐crotonamide dimethyl phosphate and its N‐methyl analog labeled with 32 P and 14 C
Author(s) -
Burton W. B.
Publication year - 1971
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.2590070203
Subject(s) - chemistry , phosphate , trimethyl phosphate , yield (engineering) , radiosynthesis , dimethyl ether , cis–trans isomerism , medicinal chemistry , nuclear chemistry , stereochemistry , organic chemistry , catalysis , materials science , in vivo , microbiology and biotechnology , metallurgy , biology
Two vinyl phosphates, 3‐hydroxy‐ N,N ‐dimethyl‐cis‐crotonamide dimethyl phosphate, and its N ‐monomethyl analog, 3‐hydroxy‐ N ‐methyl‐cis‐crotonamide dimethyl phosphate, labeled with 32 P and 14 C in three positions, have been synthesized in milligram amounts. The radiosynthesis routes are reported and the effect of reduced scale preparation is discussed. As the compounds exist in geometric isomers, methods for their separation have been developed. The purity of the cis‐isomers was determined to be 98 to 99%. The yield of 3‐hydroxy‐ N,N ‐dimethyl‐cis‐crotonamide dimethyl phosphate labeled with 32 P was 38%, with 14 C‐O‐methyl 73% and with 14 C‐ N ‐methyl 34%. The yield of 3‐hydroxy‐ N ‐methyl‐cis‐crotonamide dimethyl phosphate labeled with 32 P was 38%, with 14 C‐ O ‐methyl 73% and with 14 C‐ N ‐methyl 80%.