Preparative method of R-(-)-lbuprofen by diastereomer crystallization.
The economic and effective method for preparation of R-(-)-ibuprofen by diastereomer crystallization was developed. R-(-)-ibuprofen was resolved from racemic ibuprofen by forming R-(-)-ibuprofen-R-(+)-alpha-methylbenzylamine diastereomeric salt with R-(+)-alpha(-methylbenzylamine and crystallization. The purity of R-(-)-ibuprofen-R-(+)-alpha-methylbenzylamine diastereomeric salt was tested and confirmed using HPLC and 1H-NMR method. The pure diastereomeric salt collected from repeated recrystallization was further fractionated by liquid-liquid extraction to the pure enantiomer without racemization. R-(-)-ibuprofen was recovered producing overall yield of 2.4% with the purity more than 99.97%.
Trung
Tran Quoc
TQ
College of Pharmacy, Kangwon National University, Chunchon 200-701, Korea.
Kim
Jong Moon
JM
Kim
Kyeong Ho
KH
D002851:Chromatography, High Pressure Liquid; D003460:Crystallization; D007052:Ibuprofen / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D010627:Phenethylamines; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
D007202:Indicators and Reagents; D010627:Phenethylamines; C033198:1-phenethylamine; D007052:Ibuprofen