Patent US4133826A successfully refreshed from Google Patents.
US4133826A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Novel inversion process
Assignee: Sanofi Aventis France
•
Filing: 1977-04-22
•
Granted: 1979-01-09
•
Expires: 1997-04-22
Abstract
Abstract A process for the preparation of an ester of chiral (A) acid with an optically active (S) α-cyano-3-phenoxybenzyl alcohol by reacting an ester of chiral (A) acid with α-cyano-3-phenoxybenzyl alcohol of the formula ##STR1## in its optically active (R) form or a racemic (R,S) mixture or a mixture of esters of said (R) alcohol and (S) alcohol in non-equimolecular proportions designated herein as "ester (R+S)" with a base selected from the group consisting of ammonium hydroxide, primary, secondary and tertiary amines, quaternary ammonium compounds, liquid amines of high molecular weight, ion exchange resins of a basic character and a catalytic amount of a strong base in at least one solvent in which the ester of the (R) alcohol is soluble and in which the ester of the (S) alcohol is insoluble and recovering from the resulting medium the chiral (A) acid ester of the (S) alcohol which is insoluble.
Inventors
- 👤 Julien Warnant
- 👤 Jacques Marechal-Prost
- 👤 Philippe Cosquer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 19:56
CPC Classifications
C; C07; C07C; C07C255/00; A; A01; A01N; A01N53/00; A61; A61K; A61K31/00; A61K31/13; A61K31/135; A61K31/33; C07C255/49; C07C255/53; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/62; C07D213/63; C07D213/64; C07D213/78; C07D213/81; C07D239/00; C07D239/02; C07D239/24; C07D239/28; C07D239/32; C07D239/34; C07D241/00; C07D241/02; C07D241/10; C07D241/14; C07D241/18
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
142 words
A process for the preparation of an ester of a chiral (A) acid and (S) α-cyano-3-phenoxybenzyl alcohol comprising reacting an ester of chiral (A) acid with α-cyano-3-phenoxybenzyl alcohol of the formula ##STR7## in its optically active (R) form or a racemic (R,S) mixture or a mixture of esters of said (R) alcohol and (S) alcohol in non-equimolecular proportions with a base selected from the group consisting of ammonium hydroxide, primary, secondary and tertiary amines, quaternary ammonium compounds, liquid amines of high molecular weight, ion exchange resins of a basic character and a catalytic amount of a strong base in at least one solvent in which the ester of the (R) alcohol is soluble and in which the ester of the (S) alcohol is insoluble and recovering from the resulting medium the chiral (A) acid ester of the (S) alcohol which is insoluble.
Claim 2
Dependent Claim
142 words
A process for the preparation of an ester of a chiral (A) acid and (S) α-cyano-3-phenoxybenzyl alcohol comprising reacting an ester of chiral (A) acid with α-cyano-3-phenoxybenzyl alcohol of the formula ##STR7## in its optically active (R) form or a racemic (R,S) mixture or a mixture of esters of said (R) alcohol and (S) alcohol in non-equimolecular proportions with a base selected from the group consisting of ammonium hydroxide, primary, secondary and tertiary amines, quaternary ammonium compounds, liquid amines of high molecular weight, ion exchange resins of a basic character and a catalytic amount of a strong base in at least one solvent in which the ester of the (R) alcohol is soluble and in which the ester of the (S) alcohol is insoluble and recovering from the resulting medium the chiral (A) acid ester of the (S) alcohol which is insoluble.
Claim 3
Dependent Claim
30 words
The process of claim 1 wherein the basic agent is selected from the group consisting of ammonium hydroxide, secondary and tertiary amines and a catalytic amount of a strong base.
Claim 4
Dependent Claim
32 words
The process of claim 2 wherein the chiral (A) acid is selected from the group consisting of an acid with one asymetric carbon atom and an acid with 2 asymetric carbon atoms.
Claim 5
Dependent Claim
61 words
The process of claim 1 wherein the chiral (A) acid is selected from the group consisting of an acid with one asymetric carbon atom and an acid with 2 asymetric carbon atoms and the basic agent is selected from the group consisting of primary amines, quaternary ammonium compounds, high molecular weight liquid amines and ion exchange resins of a basic character.
Claim 6
Dependent Claim
23 words
The process of claim 2 wherein the chiral (A) acid is a cyclopropane carboxylic acid with 2 asymetric carbon atoms in the ring.
Claim 7
Dependent Claim
30 words
The process of claim 5 wherein the chiral (A) acid is a cis or trans optically active cyclopropane carboxylic acid of the formula ##STR8## wherein Hal is chlorine or bromine.
Claim 8
Dependent Claim
59 words
The process of claim 1 wherein the chiral (A) acid is a cis or trans, optically active cyclopropane carboxylic acid of the formula ##STR9## wherein Hal is chlorine or bromine and the basic agent is selected from the group consisting of primary amines, quaternary ammonium compounds, high molecular weight liquid amines and ion exchange resins of a basic character.
Claim 9
Dependent Claim
22 words
The process of claim 2 wherein the chiral (A) acid is selected from the group consisting of 2,2-dimethyl-3R-(2,2-dibromovinyl)-cyclopropane-1R-carboxylic acid and 2,2-dimethyl-3R-(2,2-dichlorovinyl)-cyclopropane-1R-carboxylic acid.
Claim 10
Dependent Claim
51 words
The process of claim 1 wherein the chiral (A) acid is selected from the group consisting of 2,2-dimethyl-3R-(2,2-dibromovinyl)-cyclopropane-1R-carboxylic acid and 2,2-dimethyl-3R-(2,2-dichlorovinyl)-cyclopropane-1R-carboxylic acid and the basic agent is selected from the group consisting of primary amines, quaternary ammonium compounds, high molecular weight liquid amines and ion exchange resins of a basic character.
Claim 11
Dependent Claim
51 words
The process of claim 2 wherein the basic agent is selected from the group consisting of ammonium hydroxide, triethylamine, diethylamine, morpholine, pyrrolidine, piperidine and a catalytic amount of a strong base selected from the group consisting of sodium hydroxide, potassium hydroxide, alkali metal alcoholates, alkali metal amides and alkali metal hydrides.
Claim 12
Dependent Claim
28 words
The process of claim 2 wherein the basic agent is selected from the group consisting of diisopropylamine, ephedrine, triethylenediamine and catalytic amounts of potassium tert.-butylate and sodium isopropylate.
Claim 13
Dependent Claim
44 words
The process of claim 1 wherein the basic agent is selected from the group consisting of benzylamine, n-butylamine, sec.-butylamine, tetrabutyl ammonium hydroxide, high molecular weight amines insoluble in water and ion exchange resins with a strongly basic character containing amines or quaternary ammonium groups.
Claim 14
Dependent Claim
24 words
The process of claim 1 wherein the solvent is selected from the group consisting of acetonitrile, alkanols and mixtures of alkanols and petroleum ether.
Claim 15
Dependent Claim
24 words
The process of claim 2 wherin the solvent is selected from the group consisting of acetonitrile, alkanols and mixtures of alkanols and petroleum ether.
Claim 16
Dependent Claim
13 words
The process of claim 2 wherein the chiral (A) acid is 2,2-dimethyl-3R-(2,2-dibromovinyl)-cyclopropane-1R-carboxylic acid.
Claim 17
Dependent Claim
70 words
The process of claim 15 wherein the solvent is selected from the group consisting of acetonitrile, alkanols and mixtures of alkanols and petroleum ether and the basic agent is selected from the group consisting of ammonium hydroxide, triethylamine, diethylamine, morpholine, pyrrolidine, piperidine and a catalytic amount of a strong base selected from the group consisting of sodium hydroxide, potassium hydroxide, alkali metal alcoholates, alkali metal amides and alkali metal hydrides.
Claim 18
Dependent Claim
47 words
The process of claim 15 wherein the solvent is selected from the group consisting of acetonitrile, alkanols and mixtures of alkanols and petroleum ether and the basic agent is selected from the group consisting of diisopropylamine, ephedrine, triethylenediamine and catalytic amounts of potassium tert.-butylate and sodium isopropylate.
Claim 19
Dependent Claim
13 words
The process of claim 1 wherein the chiral (A) acid is 2,2-dimethyl-3R-(2,2-dibromovinyl)-cyclopropane-1R-carboxylic acid.
Claim 20
Dependent Claim
44 words
The process of claim 18 wherein the basic agent is selected from the group consisting of benzylamine, n-butylamine, sec.-butylamine, tetrabutyl ammonium hydroxide, high molecular weight amines insoluble in water and ion exchange resins with a strongly basic character containing amines or quaternary ammonium groups.
Claim 21
Dependent Claim
13 words
The process of claim 2 wherein the starting ester is (R) α-cyano-3-phenoxybenzyl 2,2-dimethyl-3R-(2,2-dibromovinyl)-cyclopropane-1R-carboxylate.
Claim 22
Dependent Claim
42 words
The process of claim 1 wherein the starting ester is (R) α-cyano-3-phenoxybenzyl 2,2-dimethyl-3R-(2,2-dibromovinyl)-cyclopropane-1R-carboxylate and the basic agent is selected from the group consisting of primary amines, quaternary ammonium compounds, high molecular weight liquid amines and ion exchange resins of a basic character.
Claim 23
Dependent Claim
13 words
The process of claim 2 wherein the chiral (A) acid is 2,2-dimethyl-3R-(2,2-dichlorovinyl)-cyclopropane-1R-carboxylic acid.
Claim 24
Dependent Claim
13 words
The process of claim 1 wherein the chiral (A) acid is 2,2-methyl-3R-(2,2-dichlorovinyl)-cyclopropane-1R-carboxylic acid.
Claim 25
Dependent Claim
13 words
The process of claim 2 wherein the starting ester is (R) α-cyano-3-phenoxybenzyl 2,2-dimethyl-3R-(2,2-dichlorobinyl)-cyclopropane-1R-carboxylate.
Claim 26
Dependent Claim
42 words
The process of claim 1 wherein the starting ester is (R) α-cyano-3-phenoxybenzyl 2,2-dimethyl-3R-(2,2-dichlorovinyl)-cyclopropane-1R-carboxylate and the basic agent is selected from the group consisting of primary amines, quaternary ammonium compounds, high molecular weight liquid amines and ion exchange resins of a basic character.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-01-08 | 1982-07-10 | 1983-01-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-01-08 | 1986-07-10 | 1987-01-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-01-08 | 1990-07-10 | 1991-01-09 | $7700.00 | Window Closed / Lapsed |