Process for preparing biotin
US4044020A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Jun 30, 1975 |
| Grant date | Aug 23, 1977 |
| Priority date | — |
| Expiry date | Jun 30, 1995 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D333/36
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
Biotin is prepared by (a) ozonizing methylcyclohexene; (b) reacting nitromethane with the methyl-6-oxohexanoate from a to form 7-nitro-6 hydroxyheptanoic acid methyl ester; (c) acylating to form the corresponding 6 acyloxy compound; (d) forming a double bond at the 6 position; (e) reacting the product of d with nitroethanethiol to form dl-7-thia-6-nitromethyl-9-nitro-nonanoic acid methyl ester; (f) forming a furoxan by cyclization; (g) reducing the furoxan and acylating to form dl-2(4-carbomethoxybutyl)-3,4-bis(acylamido)-2,5-dihydro thiophene; (h) selectively hydrogenating to form the 3,4-cis-bis(acylamido)-2,5-dihydro thiophene; and (i) hydrolyzing and cyclizing to form dl-biotin. The products formed at steps (e)-(h) are novel, as are the individual steps (e), (f), (g), and (h).
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.