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Synthesis of (S)‐1‐[3‐hydroxy‐2‐(phosphonylmethoxy) propyl]‐[2‐ 14 C]cytosine ((S)‐[ 14 C] HPMPC)
Author(s) -
Haynes U. J.,
Swigor J. E.,
Bronson J. J.
Publication year - 1991
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.2580291106
Subject(s) - chemistry , cytosine , carbon 14 , medicinal chemistry , yield (engineering) , nuclear chemistry , hydroxide , organic chemistry , dna , biochemistry , physics , materials science , quantum mechanics , metallurgy
The synthesis of (S)‐[ 14 C]HPMPC ( 4 ) is described. Heating [2‐ 14 C]cytosine ( 1 ) in N, N‐dimethylformamide with (R)‐3‐0‐benzyl‐2‐0‐[(diethylphosphonyl)methyl]‐1‐0‐(methylsulfonyl) glycerol in the presence of cesium carbonate gave (S)‐1‐[3‐benzyloxy‐2‐(diethylphosphonylmethoxy) propyl]‐[2‐ 14 C]cytosine ( 2 ). Reduction with palladium hydroxide on carbon in cyclohexene yielded (S)‐1‐[3‐hydroxy‐2‐(diethylphosphonylmethoxy)propyl]‐[2‐ 14 C] cytosine ( 3 ). Deprotection of the diethylphosphonate ester with bromotrimethylsilane and treatment with water produced 190 mg of [ 14 C] HPMPC ( 4 ) having a specific activity of 21.2 μCi/mg and a radiochemical purity 98.5% in an overall yield of 5.6%.