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Preparative Method of R-(-)-lbuprofen by Diastereomer Crystallization

Preparative Method of R-(-)-lbuprofen by Diastereomer Crystallization

Tran Quoc Trung, Jong Moon Kim, Kyeong Ho Kim

Arch Pharm Res. 2006 Jan;29(1):108-11.

PMID: 16491852

Abstract:

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%.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP3886699	(R)-(+)-α-Methylbenzylamine		3886-69-9	Price

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