US4713470A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Racemization of amino acids
Assignee: Zeneca Inc
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Filing: 1985-05-22
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Granted: 1987-12-15
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Expires: 2005-05-22
Abstract
Abstract There is disclosed a process for the racemization of amino acids and derivatives thereof. The racemization process of the present invention uses an aromatic aldehyde-containing polymer made from the reaction of a hydroxy-aromatic aldehyde with a chloromethylated vinylbenzene polymer under reaction conditions to form an aromatic aldehyde-containing polymer wherein the aldehydic moiety is linked to the polymer through an ether linkage. There is also disclosed a process for the production of the racemization catalyst. Another embodiment of the invention comprises a process for the promotion of the racemization reaction wherein a tertiary amine-containing resin is used as a promoting agent.
Inventors
- 👤 Stanley B. Mirviss
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 22:18
CPC Classifications
C; C07; C07B; C07B57/00
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
87 words
A process for the racemization of an optical isomer of an alpha amino acid or derivative thereof which comprises contacting said optical isomer under conditions conductive to racemization with, as a racemization catalyst the product formed when a hydroxy aromatic aldehyde is reacted with a chloroalkyl-substituted vinylbenzene polymer wherein the number of repeating polymer units ranges from about 100 to about 1,000,000 under reaction conditions so as to form an aromatic aldehyde-containing polymer wherein the aldehyde-substituted aromatic moiety is linked to the polymer through an ether linkage.
Claim 2
Dependent Claim
87 words
A process for the racemization of an optical isomer of an alpha amino acid or derivative thereof which comprises contacting said optical isomer under conditions conductive to racemization with, as a racemization catalyst the product formed when a hydroxy aromatic aldehyde is reacted with a chloroalkyl-substituted vinylbenzene polymer wherein the number of repeating polymer units ranges from about 100 to about 1,000,000 under reaction conditions so as to form an aromatic aldehyde-containing polymer wherein the aldehyde-substituted aromatic moiety is linked to the polymer through an ether linkage.
Claim 3
Dependent Claim
15 words
The process of claim 1 wherein said optical isomer is an alpha amino acid ester.
Claim 4
Dependent Claim
16 words
The process of claim 2 wherein the amino acid ester is an ester of an arylalanine.
Claim 5
Dependent Claim
14 words
The process of claim 3 wherein said ester of an arylalanine is the D-isomer.
Claim 6
Dependent Claim
15 words
The process of claim 2 wherein said amino acid ester is an ester of phenylalanine.
Claim 7
Dependent Claim
17 words
The process of claim 2 wherein said ester is a C 1 to about C 8 ester.
Claim 8
Dependent Claim
12 words
The process of claim 2 wherein said ester is methyl or ethyl.
Claim 9
Dependent Claim
30 words
The process of claim 1 wherein said hydroxy aromatic aldehyde has the structure: ##STR6## wherein R 1 is a non-reactive substituent, and n is a number from 1 to 3.
Claim 10
Dependent Claim
12 words
The process of claim 8 wherein said hydroxy aromatic aldehyde is salicylaldehyde.
Claim 11
Dependent Claim
12 words
The process of claim 8 wherein said hydroxy aromatic aldehyde is 3,4-dihydroxybenzaldehyde.
Claim 12
Dependent Claim
12 words
The process of claim 8 wherein said hydroxy aromatic aldehyde is 5-nitrosalicylaldehyde.
Claim 13
Dependent Claim
13 words
The process of claim 1 wherein said chloroalkyl-substituted vinylbenzene polymer is poly(vinylbenzyl chloride).
Claim 14
Dependent Claim
16 words
The process of claim 1 wherein said chloroalkyl-substituted vinylbenzene polymer is poly(vinylbenzyl chloride) crosslinked with divinylbenzene.
Claim 15
Dependent Claim
13 words
The process of claim 1 wherein said racemization catalyst has the structure: ##STR7##
Claim 16
Dependent Claim
23 words
The process of claim 1 wherein said hydroxy aromatic aldehyde is reacted with a chloroalkyl-substituted vinylbenzene polymer in the presence of a base.
Claim 17
Dependent Claim
13 words
The process according to claim 15 wherein the hydroxy aromatic aldehyde is salicylaldehyde.
Claim 18
Dependent Claim
14 words
The process according to claim 15 wherein the chloroalkyl-substituted vinylbenzene polymer is poly(vinylbenzyl chloride).
Claim 19
Dependent Claim
17 words
The process according to claim 15 wherein the chloroalkyl-substituted vinylbenzene polymer is poly(vinylbenzyl chloride) crosslinked with divinylbenzene.
Claim 20
Dependent Claim
25 words
The process according to claim 15 wherein the base is selected from the group consisting of potassium hydroxide, sodium hydroxide, pyridine, triethylamine and lithium hydroxide.
Claim 21
Dependent Claim
53 words
The process according to claim 1 optionally comprising the use of a tertiary amine-containing resin of the formula: ##STR8## wherein A and R 1 are independently alkyl, alkenyl, alkynyl, aryl, alkaryl or aralkyl and n is a number from about 100 to about 1,000,000 as a promoting agent for said aromatic aldehyde-containing polymer.
Claim 22
Dependent Claim
29 words
The process according to claim 20 wherein said tertiary amine containing resin has the structure: --CH.sub.2 --CH(C.sub.6 H.sub.4 CH.sub.2 N(CH.sub.3).sub.2)--.sub.n wherein n is an integer from 100 to 1,000,000.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-12-14 | 1991-06-15 | 1991-12-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-12-14 | 1995-06-15 | 1995-12-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-12-14 | 1999-06-15 | 1999-12-15 | $7700.00 | Window Closed / Lapsed |