Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1981-01-28
1982-06-08
Love, Ethel G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C07D33714
Patent
active
043340776
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##
REFERENCES:
patent: 3509154 (1970-04-01), Fouche
patent: 4104280 (1978-08-01), Ackrell
patent: 4237160 (1980-12-01), Hamel et al.
Chem. Abstracts 91:140734w.
Belanger Patrice C.
Rokach Joshua
Scheigetz John
Young Robert N.
Arther Thomas E.
Love Ethel G.
Merck & Co. , Inc.
Pfeiffer Hesna J.
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