Stereospecific sulfoxidation of dibenzo thiepins
US4334077A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Jan 28, 1981 |
| Grant date | Jun 8, 1982 |
| Priority date | — |
| Expiry date | Jan 28, 2001 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D337/14
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
The present invention relates to a process for the preparation of an enantiomer of 7 or 8-fluoro-dibenzo[b,f]thiepin-3-carboxylic acid having a negative rotation and prostaglandin antagonist activity. The process involves preparation and separation of novel diastereoisomeric esters of 10-hydroxy-7 or 8 fluro-dibenzothiepin-3 carboxylic acid ester followed by stereospecific sulfoxidation of the selected diastereoisomer to produce the corresponding novel sulfoxide having a preponderance of the desired configuration of the sulfoxide entity followed by treatment of the product with a strong base to produce directly the desired (-)7 or 8 fluoro-dibenzo[b,f]thiepin-3 carboxylic acid 5-oxide having the structural formula shown below: ##STR1##
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.