Substituted 2-[-6-benzyl-5-oxo-3-phenyl-(3s,7s, 7aR)-perhydroimidazol[1,5-c][1,3]thiazol-7yl] compounds
AssigneeCouncil of Scientific and Industrial Research
InventorsSubhash Prataprao Chavan, Amar Gopal Chittiboyina, Subhash Krishnaji Kamat, Uttam Ramrao Kalkote, Thotapallil Ravindranathan
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Abstract
A novel route has been developed for substituted 2-[-6-benzyl-5-oxo-3-phenyl-(3s,7s,7aR)-perhydroimidazol[1,5-c][1,3]thiazol] compounds; crucial intermediates for D(+)-biotin of formula (7) which involves simple, efficient, practical and cost effective protocol. These are crucial intermediates for commercially important D(+)-biotin preparation. These compounds are more stable and are produced by non-hazardous methods.
Claims16
A substituted 2-[-6-benzyl-5-oxo-3-phenyl-(3s,7s,7aR)-perhydroimidazol[1,5-c][1,3]thiazol] of formula (7):
- wherein R=benzyl, and R1=a member selected from the group consisting of 1-phenyl-1-ethanone, 1-(4-chlorophenyl)-1-ethanone, 1-(4-methoxypheny)-1-ethanone, 2-oxocyclohexyl, 1-trimethylsilyloxy-2-oxocyclohexyl, allyl, 1-hexanyl, 4-dimethylaminophenyl, and 2-methylpropanoate.
A process for the preparation of compounds having formula 7
- wherein R=benzyl, and R1=a member selected from the group consisting of 1-phenyl-1-ethanone, 1-(4-chlorophenyl)-1-ethanone, 1-(4-methoxypheny)-1-ethanone, 2-oxocyclohexyl, 1-trimethylsilyloxy-2-oxocyclohexyl, allyl, 1-hexanyl, 4-dimethylaminophenyl, and 2-methylpropanoate, said process comprising:
- a) reacting compound of formula 6
- with Lewis acid and a nucleophilic agent at a temperature ranging between 0° to 30° C. in an organic solvent for 10-30 minutes,
- b) quenching the reaction mixture with either water or saturated alkaline aqueous solution as quenching agent,
- c) separating and concentrating the organic layer,
- d) purifying to obtain compound of formula (7).
A process for the preparation of keto acid formula (1):
- said process comprising:
- a) reacting a compound having formula
- 7e) 6 benzyl-7-(1-trimethylsilyloxy-2-oxocyclohexyl)-3-phenyl-(3S, 7S, 7aR)-perhydroimidazo[1,5-c][1,3 ]thiazol-5-one, or
- 7e′) 6 benzyl-7-(1-hydroxy-2-oxocyclohexyl)-3-phenyl-(3S, 7S, 7aR)-perhydroimidazo[1,5-c][1,3 ]thiazol-5-one,
- with an oxidizing agent in presence of alkaline alcohol at temperature ranging between 15-40° C. for the period of 30-90 min,
- b) removing the alcohol and extracting with an organic solvent,
- c) separating the aqueous layer and acidifying to pH 4.0 to 5.0,
- d) further extracting the mixture with an organic solvent,
- e) separating and concentrating the solvent layer,
- f) removing the solvent to obtain compound of formula (1), and optionally,
- g) converting the compound of formula (1) to obtain D(+) biotin.
Dependencies are inferred from the claim text.