US4048224A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for resolving alanine, 3-fluoro and 2-deutero-3-fluoro-DL-alanine
Assignee: Merck and Co Inc
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Filing: 1976-03-05
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Granted: 1977-09-13
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Expires: 1996-03-05
Abstract
Abstract DL-Alanine, 3-fluoro-DL-alanine and 2-deutero-3-fluoro-DL-alanine, are resolved by reaction with a resolving base and a β-dicarbonyl compound. The resulting azomethine diastereomeric salts which are easily separated, the masking group is readily removed under mildly acidic conditions.
Inventors
- 👤 John M. Chemerda
- 👤 George Gal
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 13:44
CPC Classifications
C; C07; C07C; C07C227/00; C07C227/14; C07C227/18; C07C227/30; C07C227/34; C07C229/00; C07C229/02; C07C229/04; C07C229/06; C07C229/08; C07C229/22; C07C229/34; C07C229/36; C07C237/00; C07C237/02; C07C237/04; C07C237/06; C07C51/00; C07C51/42; C07C51/487; C07B; C07B2200/00; C07B2200/07
Claims Analysis
Total Claims: 6
Claim 1
Independent Claim
107 words
The process for resolving a DL-mixture of an alanine compound which is alanine, 3-fluoroalanine, or 2-deutero-3-fluoro alanine which comprises reacting approximately equimolar amounts of the alanine compound, a resolving base which is quinine, quinidine, brucine, strychnine, d-α,N,N-trimethylbenzylamine, or 1-α,N,N-trimethylbenzylamine, and a β-dicarbonyl compound of the formula ##STR2## wherein R is methyl, phenyl or alkoxy of 1-5 carbon atoms, in a solution of a lower alkanol of 1-5 carbon atoms at reflux for 1/2-3 hours, and separating the salt parts of the diastereomers by crystallization, then treating both separately, first with an alkali metal hydroxide, then with H 3 O + , and recovering the respective individual isomers.
Claim 2
Dependent Claim
107 words
The process for resolving a DL-mixture of an alanine compound which is alanine, 3-fluoroalanine, or 2-deutero-3-fluoro alanine which comprises reacting approximately equimolar amounts of the alanine compound, a resolving base which is quinine, quinidine, brucine, strychnine, d-α,N,N-trimethylbenzylamine, or 1-α,N,N-trimethylbenzylamine, and a β-dicarbonyl compound of the formula ##STR2## wherein R is methyl, phenyl or alkoxy of 1-5 carbon atoms, in a solution of a lower alkanol of 1-5 carbon atoms at reflux for 1/2-3 hours, and separating the salt parts of the diastereomers by crystallization, then treating both separately, first with an alkali metal hydroxide, then with H 3 O + , and recovering the respective individual isomers.
Claim 3
Dependent Claim
12 words
The process of claim 1 in which quinine is the resolving base.
Claim 4
Dependent Claim
10 words
The process of claim 1 in which R is methyl.
Claim 5
Dependent Claim
12 words
The process of claim 1 in which the alanine compound is DL-3-fluoroalanine.
Claim 6
Dependent Claim
12 words
The process of claim 1 in which the alanine compound is DL-2-deutero-β-fluoroalanine.
References Cited (Backward Citations)
US3028395A
Cited
US3381031A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-09-12 | 1981-03-14 | 1981-09-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-09-12 | 1985-03-14 | 1985-09-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-09-12 | 1989-03-14 | 1989-09-13 | $7700.00 | Window Closed / Lapsed |