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Home   •   Spotlight  •  rlist4q05j  •  Most Requested Journal Articles 4Q05-Chemistry and Related Science (8)

200602j8Most Requested Journal Articles 4Q05-Chemistry and Related Science

Following is one of the journal articles most requested by researchers using CAS electronic products.

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CAS indexed 21 chemical substances from this document. CAS subject entries for this document include: Bond cleavage; Ring opening; Sulfonylation; and 4 additional concepts.

CAPLUS COPYRIGHT 2006 ACS on STN

TITLE:	Research and Development of a Second-Generation Process for Oseltamivir Phosphate, Prodrug for a Neuraminidase Inhibitor
AUTHOR(S):	Harrington, Peter J.; Brown, Jack D.; Foderaro, Tommaso; Hughes, Robert C.
CORPORATE SOURCE:	Boulder Technology Center, Roche Colorado Corporation, Boulder, CO, 80301, USA
SOURCE:	Organic Process Research & Development (2004), 8(1), 86-91 CODEN: OPRDFK; ISSN: 1083-6160
PUBLISHER:	American Chemical Society
LANGUAGE:	English

ABSTRACT:
A second-generation manufg. process from a shikimic acid-derived epoxide to oseltamivir phosphate features a magnesium chloride-amine complex-catalyzed ring opening of the epoxide by tert-butylamine, a selective O-sulfonylation of the resulting tert-butylamino alc., a surprisingly efficient cleavage of a tert-Bu group from an aliph. tert-butylamide, and the isolation of oseltamivir phosphate from a palladium-catalyzed allyl transfer reaction mixt. The overall yield from the epoxide to oseltamivir phosphate was increased from 27 to 29% or 35-38% for two previous processes, resp., to 61%.