Process for the production of (+) biotin
US4876350A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Dec 16, 1987 |
| Grant date | Oct 24, 1989 |
| Priority date | — |
| Expiry date | Dec 16, 2007 |
Classification
- Technology area (CPC Y)Emerging Cross-Sectional Technologies
- CPC primaryY02P20/55
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
Process for the production of (+) biotin. A compound of the formula: ##STR1## wherein R.sub.1 is e.g., an (R)-1-phenylalkyl group, and R.sub.2 is, e.g., hydrogen. The desired diastereomer of the formula: ##STR2## is separated out. If R.sub.2 is H, a protective group is introduced by reaction with, e.g., an aliphatic acid chloride. The diastereomer is converted by reaction with a thiocarboxylic acid salt derivative into the corresponding thiolacetone, which is reacted with a Grignard reactant and subsequently water is split off. Alternatively, the corresponding thiolacetone is reacted with a compound of the formula: EQU (C.sub.6 H.sub.5).sub.3 P.sup..sym. (CH.sub.2).sub.4 COOR.sub.3.X.sup..crclbar. wherein R.sub.3 is, e.g., H, and X is a halogen atom, in the presence of a base to provide a compound of the formula: ##STR3## Such compound is catalytically hydrogenated and then converted into (+) biotin by cleavage of the protective groups.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.