US4461835A
Expired / Lapsed
US
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Process for preparing optically-active isoprenoid intermediates
Assignee: Wisconsin Alumni Research Foundation
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Filing: 1982-07-02
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Granted: 1984-07-24
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Expires: 2002-07-02
Abstract
Abstract The invention discloses a method for preparing optically active bifunctional synthons useful in synthesizing natural isoprenodis by resolving racemic substituted aryloxy- alpha -alkyl esters through the hydrolytic action of microorganisms selected from the orders Endomycetales and Eubacteriales.
Inventors
- 👤 Charles J. Sih
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 21:05
CPC Classifications
C; C12; C12P; C12P41/00; C12P41/003; C12P41/005; C12P7/00; C12P7/40; Y; Y10; Y10S; Y10S435/00; Y10S435/8215; Y10S435/822; Y10S435/874
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
58 words
A process for preparing optically active bifunctional synthons which comprises revolving aryloxy-α-alkyl esters by exposing said esters in aqueous medium to the hydrolytic action of the carboxyesterases elaborated by a microorganism of the orders Endomycetales and Eubacteriales whereby one antipode of said esters is hydrolyzed to give optically active aryloxy-α-methyl acids and recovering the component optically active isomers.
Claim 2
Dependent Claim
58 words
A process for preparing optically active bifunctional synthons which comprises revolving aryloxy-α-alkyl esters by exposing said esters in aqueous medium to the hydrolytic action of the carboxyesterases elaborated by a microorganism of the orders Endomycetales and Eubacteriales whereby one antipode of said esters is hydrolyzed to give optically active aryloxy-α-methyl acids and recovering the component optically active isomers.
Claim 3
Dependent Claim
13 words
The process of claim 1 wherein the racemic ester is an aryloxy-α-methyl ester.
Claim 4
Dependent Claim
12 words
The process of claim 1 wherein the racemic ester is aryloxy-α-ethyl ester.
Claim 5
Dependent Claim
13 words
The process of claim 1 wherein the racemic ester is an aryloxy-α-propyl ester.
Claim 6
Dependent Claim
28 words
The process of claim 1 wherein the microorganism for effecting the resolution is selected from Enterobacter cloacae NRRL B-15052, Bacillus sp. NRRL B-15053 or Saccharomyces aureofaciens NRRL Y-7253.
Claim 7
Dependent Claim
18 words
The process of claim 1 wherein the microbiological resolution is effected in a growing culture of the microorganism.
Claim 8
Dependent Claim
23 words
The process of claim 1 wherein the microbiological resolution is effected in a microorganism-free medium containing the hydrolytic enzyme elaborated by the microorganism.
Claim 9
Dependent Claim
17 words
The process of claim 1 wherein the microbiological resolution is effected by immobilized cells of the microorganism.
Claim 10
Dependent Claim
65 words
A process for preparing (-)4-aryloxy-2-methylbutyric acid and (+)4-aryloxy-2-methylbutyric acid which comprises cultivating a microorganism selected from the order Endomycetales and Eubacteriales, in an aqueous mutrient medium, under submerged aerobic conditions, in the presence of a compound having the formula ##STR5## where R 1 is methyl, ethyl or propyl and R 2 is benzyl, nitrobenzyl, chlorobenzyl, bromobenzyl or phenacyl and recovering the component optically active isomers.
Claim 11
Dependent Claim
65 words
A process for preparing (-)4-aryloxy-2-methylbutyric acid and (+)4-aryloxy-2-methylbutyric acid which comprises cultivating a microorganism selected from the order Endomycetales and Eubacteriales, in an aqueous mutrient medium, under submerged aerobic conditions, in the presence of a compound having the formula ##STR5## where R 1 is methyl, ethyl or propyl and R 2 is benzyl, nitrobenzyl, chlorobenzyl, bromobenzyl or phenacyl and recovering the component optically active isomers.
Claim 12
Dependent Claim
39 words
The process of claim 6 wherein the substrate subjected to microbiological resolution is selected from the group consisting of methyl, ethyl and propyl esters of (±)4-benzyloxy-2-methylbutyric acid and the component optically active isomers are recovered from the fermentation medium.
Claim 13
Dependent Claim
39 words
The process of claim 6 wherein the substrate subjected to microbiological resolution is selected from the group consisting of methyl, ethyl and propyl esters of (±)4-ρ-nitrobenzyloxy-2-methyl-butyric acid and the component optically active isomers are recovered from the fermentation medium.
Claim 14
Dependent Claim
39 words
The process of claim 6 wherein the substrate subjected to microbiological resolution is selected from the group consisting of methyl, ethyl and propyl esters of (±)4-phenacyloxy-2-methylbutyric acid and the component optically active isomers are recovered from the fermentation medium.
Claim 15
Dependent Claim
39 words
The process of claim 6 wherein the substrate subjected to microbiological resolution is selected from the group consisting of methyl, ethyl and propyl esters of (±)4-ρ-bromobenzyloxy-2-methylbutyric acid and the component optically active isomers are recovered from the fermentation medium.
Claim 16
Dependent Claim
39 words
The process of claim 6 wherein the substrate subjected to microbiological resolution is selected from the group consisting of methyl, ethyl and propyl esters of (±)4-o-chlorobenzyloxy-2-methylbutyric acid and the component optically active isomers are recovered from the fermentation medium.
Claim 17
Dependent Claim
39 words
The process of claim 6 wherein the substrate subjected to microbiological resolution is selected from the group consisting of methyl, ethyl and propyl esters of (±)4-ρ-chlorobenzyloxy-2-methylbutyric acid and the component optically active isomers are recovered from the fermentation medium.
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) | 1987-07-24 | 1988-01-23 | 1988-07-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-07-24 | 1992-01-23 | 1992-07-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-07-24 | 1996-01-23 | 1996-07-24 | $7700.00 | Window Closed / Lapsed |