Regioselective chlorination of 6-(5-methyl-2-oxo-4-imidazolin-4-yl)-6-oxohexanoic acid ethyl ester: A new synthesis of biotin

doi:10.1007/s11094-006-0215-3

Paper

Regioselective chlorination of 6-(5-methyl-2-oxo-4-imidazolin-4-yl)-6-oxohexanoic acid ethyl ester: A new synthesis of biotin

Published Dec 1, 2006 · S. I. Zav'yalov, L. Kulikova, O. V. Dorofeeva

Pharmaceutical Chemistry Journal

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Abstract

Regioselective chlorination of a methyl group in 6-(5-methyl-2-oxo-4-imidazolin-4-yl)-6-oxohexanoic acid ethyl ester via reaction with sulfuryl chloride in methylene chloride has been performed for the first time. The synthesis of 5-(2-oxo-2,3-dihydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acid methyl and ethyl esters (tetradehydrobiotin esters) – key compounds in biotin (vitamin H) synthesis – has been developed proceeding from 6-(2-oxo-5-chloromethyl-4-imidazolin-4-yl)-6-oxohexanoic acid ester.

Study Snapshot

Regioselective chlorination of a methyl group in 6-(5-methyl-2-oxo-4-imidazolin-4-yl)-6-oxohexanoic acid ethyl ester allows for the synthesis of biotin (vitamin H).

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Regioselective chlorination of 6-(5-methyl-2-oxo-4-imidazolin-4-yl)-6-oxohexanoic acid ethyl ester: A new synthesis of biotin

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