Optically active N-.alpha.-fluoroacryloylamino acid derivatives for the resolution of racemates

• US 5,354,884 A
• Filed: 10/01/1992
• Issued: 10/11/1994
• Est. Priority Date: 07/03/1990
• Status: Expired due to Term

• Current Assignee: Daicel Chemical Industries Limited (Daicel Corporation)
• Original Assignee: Bayer AG
• Inventors: Grosser, Rolf, Arlt, Dieter, Lange, Walter, Bielefeldt, Dietmar, Bomer, Bruno
• Primary Examiner(s): Rizzo, Nicholas S.
• Assistant Examiner(s): Gupta, Yogendra N.
• Application Number:
  US07/955,225
• Time in Patent Office: 740 Days
• Field of Search: 540/608, 546/225, 546/245, 548/530, 558/14, 558/254, 560/41, 560/39, 560/43, 560/40, 560/121, 560/122, 560/123, 560/124, 560/126, 560/128, 560/155, 560/170, 564/152, 564/155, 564/156, 564/160
• US Class Current: 560/41
• CPC Class Codes: B01D 15/3833 Chiral chromatography
• CPC Class Codes: B01J 20/261 obtained by reactions only involving carbon to carbon unsaturated bonds macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds per se C08F
• CPC Class Codes: B01J 20/265 modified or post-treated polymers polymer carriers or substrates subjected to further impregnating or coating B01J20/3208
• CPC Class Codes: B01J 20/285 based on polymers
• CPC Class Codes: B01J 20/29 Chiral phases
• CPC Class Codes: B01J 20/327 Polymers obtained by reactions involving only carbon to carbon unsaturated bonds
• CPC Class Codes: B01J 2220/54 Sorbents specially adapted for analytical or investigative chromatography
• CPC Class Codes: C07C 233/49 having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
• CPC Class Codes: C07C 2601/14 The ring being saturated
• CPC Class Codes: C07C 2602/42 the bicyclo ring system containing seven carbon atoms
• CPC Class Codes: C08F 20/54 Amides , e.g. N,N-dimethylacrylamide or N-isopropylacrylamide

Abstract

α-Fluoro-substituted N-acryloylamino acid derivatives of the formula ##STR1## are used to make polymers optionally for chromatographic resolution of racemates into their enantiomers. The fluorine atom improves performance in many instances.

Claims

1. An N-α

-fluoroacryloylamino acid derivative of the formula ##STR10## wherein A is hydrogen or phenyl, and

Y is lower alkyl of 2 to 4 carbon atoms, ##STR11## provided that when A is hydrogen Y is not lower alkyl of 2 to 4 carbon atoms.

2. A compound according to claim 1, wherein such compound is N-fluoroacryloyl-L-phenylalanine ethyl ester of the formula ##STR12##

3. A compound according to claim 1, wherein such compound is N-fluoroacryloyl-L-alanine d-menthyl ester of the formula ##STR13##

4. A compound according to claim 1, wherein such compound is N-fluoroacryloyl-L-alanine 1-bornyl ester of the formula ##STR14##

5. A compound according to claim 1, wherein such compound is N-fluoroacryloyl-L-alanine (+)-fenchyl ester of the formula ##STR15##