EP 1461332 A4 20091021 - PRODUCTION OF CHIRALLY PURE ALPHA-AMINO ACIDS AND N-SULFONYL ALPHA-AMINO ACIDS
Title (en)
PRODUCTION OF CHIRALLY PURE ALPHA-AMINO ACIDS AND N-SULFONYL ALPHA-AMINO ACIDS
Title (de)
HERSTELLUNG VON ENANTIOMERENREINEN ALPHA-AMINOSÄUREN UND N-SULFONYL-ALPHA-AMINOSÄUREN
Title (fr)
PRODUCTION D'ACIDES ALPHA-AMINES ET D'ACIDES ALPHA-AMINES N-SULFONYLES CHIRALEMENT PURS
Publication
Application
Priority
- US 0238117 W 20021126
- US 1430401 A 20011211
- US 16689602 A 20020611
Abstract (en)
[origin: WO03050062A2] Methods for production of chirally pure alpha -amino acids and N-sulfonyl alpha -amino acids are described. An aldehyde and a cyanide salt are reacted with an alpha -methylbenzylamine to afford a product. The product reacts with a strong acid, is neutralized, and is extracted. The resulting product is subsequently hydrogenated and hydrolyzed to provide a product which is dissolved in a strong acid to provide a salt of a chirally pure alpha -amino acid, which is reacted to provide the chirally pure alpha -amino acid. Another method involves mixing ephedrine hemihydrate and an N-sulfonyl alpha -ethylnorvaline in ethanol at a molar ratio of 1:1; heating the mixture to dissolve the solids; cooling to allow formation of a precipitate; washing with an organic solvent to give diastereomeric salt; recrystallizing the salt; dissolving the recrystallized salt in an organic solvent and strong aqueous acid, separating the layers; washing the organic extract; drying and concentrating to provide chirally pure N-sulfonyl alpha -amino acid.
IPC 8 full level
A61P 25/28 (2006.01); C07B 53/00 (2006.01); C07B 57/00 (2006.01); C07C 213/00 (2006.01); C07C 215/08 (2006.01); C07C 227/18 (2006.01); C07C 227/26 (2006.01); C07C 227/32 (2006.01); C07C 229/08 (2006.01); C07D 233/66 (2006.01); C07D 277/32 (2006.01); C07D 307/64 (2006.01); C07D 333/34 (2006.01); C07D 409/12 (2006.01)
IPC 8 main group level
C07C (2006.01)
CPC (source: EP)
A61P 25/28 (2017.12); C07D 307/64 (2013.01); C07D 333/34 (2013.01); C07D 409/12 (2013.01)
Citation (search report)
- [Y] EP 0326934 A1 19890809 - BASF AG [DE]
- [Y] WO 0109084 A1 20010208 - EASTMAN CHEM CO [US]
- [XY] J.C. SPEELMAN ET AL, J. ORG. CHEM., vol. 54, no. 5, 1989, pages 1055 - 1062, XP002542789
- [Y] T. INABA ET AL, J. ORG. CHEM., vol. 56, no. 3, 1991, pages 1274 - 1279, XP002542836
- See references of WO 03050062A2
Designated contracting state (EPC)
AT BE BG CH CY CZ DE DK EE ES FI FR GB GR IE IT LI LU MC NL PT SE SK TR
Designated extension state (EPC)
AL LT LV MK RO
DOCDB simple family (publication)
WO 03050062 A2 20030619; WO 03050062 A3 20031120; AU 2002351170 A1 20030623; AU 2002351170 B2 20090924; AU 2002351170 B8 20091008; AU 2009251195 A1 20100121; CA 2470111 A1 20030619; EP 1461332 A2 20040929; EP 1461332 A4 20091021; JP 2005511727 A 20050428; JP 4615861 B2 20110119; MX PA04005366 A 20040927; TW 200306292 A 20031116; TW I260316 B 20060821
DOCDB simple family (application)
US 0238117 W 20021126; AU 2002351170 A 20021126; AU 2009251195 A 20091224; CA 2470111 A 20021126; EP 02786817 A 20021126; JP 2003551090 A 20021126; MX PA04005366 A 20021126; TW 91135621 A 20021210