Title:
INDUSTRIALLY APPLICABLE PROCESS FOR THE SULFAMOYLATION OF ALCOHOLS AND PHENOLS
Document Type and Number:
WIPO Patent Application WO2003053992
Kind Code:
A3
Abstract:
This invention describes a safe method for the production of sulfamoyl chloride from chlorosulfonyl isocyanate and formic acid in the presence of a amide catalyst, taming the hazardous nature of this reaction by circumventing heat accumulation processes, as well as the sulfamoylation of alcohols and phenols with the resulting sulfamoyl chloride in N,N-dimethyl acetamide or N-methyl pyrrolidone thereby avoiding the formation of side-products which were inevitable with the methods of the prior art using dimethyl formamide or dichloromethane as a solvent. The current invention allows industrial scale applications and describes as an example the process of manufacture of the biologically active compound 17 beta -Hydroxyestra-1,3,5(10)-triene-3-yl sulfamate.
Inventors:
GEISLER JENS
SCHNEIDER FRANK
LOVIS KAI
LOPEZ HOLGUIN FERNANDO
SCHNEIDER FRANK
LOVIS KAI
LOPEZ HOLGUIN FERNANDO
Application Number:
PCT/EP2002/014487
Publication Date:
January 29, 2004
Filing Date:
December 18, 2002
Export Citation:
Assignee:
SCHERING AG (DE)
International Classes:
C01B21/096; C07C303/34; C07J41/00; C07C307/02; (IPC1-7): C07J41/00; C07C303/34; C07C307/02
Domestic Patent References:
| WO2000066095A2 | 2000-11-09 |
Foreign References:
| EP0403185A2 | 1990-12-19 |
Other References:
M. OKADA, ET AL.: "Efficient general method for sulphamoylation of a hydroxyl group", TETRAHEDRON LETTERS, vol. 41, no. 36, September 2000 (2000-09-01), ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, pages 7047 - 7051, XP004208258, ISSN: 0040-4039
S. SCHWARZ, ET AL.: "Synthesis of oestrogen sulphamates: compounds with a novel endocrinological profile", STEROIDS, vol. 61, no. 12, 1 December 1996 (1996-12-01), ELSEVIER SCIENCE PUBLISHERS, NEW YORK, NY, US, pages 710 - 717, XP004016631, ISSN: 0039-128X
J. ROMER, ET AL.: "Preparation and characterisation of the sulphamates of oestra-3,17xi-diols. Rapid conversion of 16alpha-fluoro-oestradiol into 16alpha- fluoro-oestradiol-3,17beta-disulphamate", JOURNAL FÜR PRAKTISCHE CHEMIE, vol. 341, no. 6, 1999, WILEY VCH, WEINHEIM, DE, pages 574 - 583, XP002182695, ISSN: 1436-9966
R. APPEL, ET AL.: "Hydrazinsulfonsäure-amide, I. Über das Hydrazodisulfamid", CHEMISCHE BERICHTE, vol. 91, 1958, VERLAG CHEMIE GMBH., WEINHEIM, DE, pages 1339 - 1341, XP008017895
S. SCHWARZ, ET AL.: "Synthesis of oestrogen sulphamates: compounds with a novel endocrinological profile", STEROIDS, vol. 61, no. 12, 1 December 1996 (1996-12-01), ELSEVIER SCIENCE PUBLISHERS, NEW YORK, NY, US, pages 710 - 717, XP004016631, ISSN: 0039-128X
J. ROMER, ET AL.: "Preparation and characterisation of the sulphamates of oestra-3,17xi-diols. Rapid conversion of 16alpha-fluoro-oestradiol into 16alpha- fluoro-oestradiol-3,17beta-disulphamate", JOURNAL FÜR PRAKTISCHE CHEMIE, vol. 341, no. 6, 1999, WILEY VCH, WEINHEIM, DE, pages 574 - 583, XP002182695, ISSN: 1436-9966
R. APPEL, ET AL.: "Hydrazinsulfonsäure-amide, I. Über das Hydrazodisulfamid", CHEMISCHE BERICHTE, vol. 91, 1958, VERLAG CHEMIE GMBH., WEINHEIM, DE, pages 1339 - 1341, XP008017895
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