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US5698741A
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Asymmetric synthesis of (-)6-chloro-4-cyclopropyl-ethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one
Assignee: Merck Sharp & Dohme LLC
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Filing: 1996-07-15
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Granted: 1997-12-16
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Expires: 2016-07-15
Abstract
Abstract An improved synthesis of a highly potent HIV reverse transcription inhibitor is disclosed, involving an acetylide and a trifluoromethyl ketone which produces a chiral product in the presence of a chiral amino alcohol.
Inventors
- 👤 Andrew S. Thompson
- 👤 Edward G. Corley
- 👤 Edward J. J. Grabowski
- 👤 Nobuyoshi Yasuda
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 11:52
CPC Classifications
C; C07; C07D; C07D265/00; C07D265/04; C07D265/12; C07D265/14; C07D265/18; C07C; C07C213/00; C07C215/00; C07C215/68; C07C215/70; C07C217/00; C07C217/54; C07C217/56; C07C217/58; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 4
Claim 1
Independent Claim
49 words
A compound of the structure ##STR35## wherein P is an amino protecting group selected from the group consisting of: benzyl, unsubstituted or substituted with C 1 -C 4 alkyl; p-methoxybenzyl; p-nitrobenzyl; p-chlorobenzyl; 2,4-dichlorobenzyl;. 2,4-dimethoxybenzyl; 4-methylsulfinylbenzyl; 9-anthrylmethyl; diphenylmethyl, and N-trialkylsilyl, wherein alkyl is defined as C 1 -C 4 alkyl.
Claim 2
Dependent Claim
49 words
A compound of the structure ##STR35## wherein P is an amino protecting group selected from the group consisting of: benzyl, unsubstituted or substituted with C 1 -C 4 alkyl; p-methoxybenzyl; p-nitrobenzyl; p-chlorobenzyl; 2,4-dichlorobenzyl;. 2,4-dimethoxybenzyl; 4-methylsulfinylbenzyl; 9-anthrylmethyl; diphenylmethyl, and N-trialkylsilyl, wherein alkyl is defined as C 1 -C 4 alkyl.
Claim 3
Dependent Claim
8 words
A compound N-(4-methoxybenzyl)-6-chloro-2- (R)-cyclopropylethynyl-hydroxy-trifluoromethyl!-methyl-aniline, of the structure ##STR36##
Claim 4
Dependent Claim
8 words
A compound N-(4-methoxybenzyl)-6-chloro-2- (R)-cyclopropylethynyl-hydroxy-trifluoromethyl!-methyl-aniline, of the structure ##STR36##
References Cited (Backward Citations)
EP0582455A1
Cited
US5519021A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 2000-12-15 | 2001-06-16 | 2001-12-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2004-12-15 | 2005-06-16 | 2005-12-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2008-12-15 | 2009-06-16 | 2009-12-16 | $7700.00 | Window Closed / Lapsed |