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A practical synthesis of ethyl 1,2,4‐triazole‐3‐carboxylate and its use in the formation of chiral 1′,2′‐ seco ‐nucleosides of ribavirin
Author(s) -
Vemishetti Purushotham,
Leiby Robert W.,
Abushanab Elie,
Panzica Raymond P.
Publication year - 1988
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570250253
Subject(s) - chemistry , carboxylate , amide , alkylation , ribavirin , hydrochloride , 1,2,4 triazole , organic chemistry , combinatorial chemistry , stereochemistry , medicinal chemistry , catalysis , biochemistry , genotype , gene
A practical and efficient synthesis of ethyl 1,2,4‐triazole‐3‐carboxylate ( 6a , R' = H) from ethyl carboethoxyformimidate hydrochloride ( 7 ) is described. Alkylation of this heterocycle with the chloromethyl ethers of 1,3‐ O ‐dibenzylbutane‐1,2 R ,3 S ‐triol ( 8a ) and 1,3,4‐ O ‐tribenzylbutane‐1,2 R ,3 S ,4‐tetrol ( 8b ), followed by conversion of the ester function to the amide and deprotection, furnished the chiral 1′,2′‐ seco ‐nucleosides of ribavirin, 11a and 11b , respectively.