Synthesis, Resolution, and Enantiomeric Purity Assay of 2-n-Butylbutanedioic Acid 4-t-Butyl Esters

Chemical Research in Chinese Universities ›› 2006, Vol. 22 ›› Issue (5): 584-588.doi:

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Synthesis, Resolution, and Enantiomeric Purity Assay of 2-n-Butylbutanedioic Acid 4-t-Butyl Esters

ZHANG Da-tong¹, TANG Li-da¹, DUAN Gui-yun¹, ZHAO Gui-long¹, XU Wei-ren², MENG Li-juan¹ and WANG Jian-wu¹

1. School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. China;
2. The Pharmaceutical Research Institute of Tianjin, Tianjin 300193, P. R. China

Received:2005-10-08 Revised:1900-01-01 Online:2006-09-25 Published:2006-09-25
Contact: WANG Jian-wu E-mail:jwwang@sdu.edu.cn

Abstract

Abstract: Racemic 2-n-butylbutanedioic acid 4-t-butyl esters were synthesized from methyl hexanoate and t-butyl α-iodoacetate via alkylation and subsequently selective hydrolyzation. The (R)- and (S)-2-n-butylbutanedioic acid 4-t-butyl esters were obtained by the resolution of the above-mentioned racemic compounds with (S)-(-) or (R)-(+)-α-methylbenzylamine, respectively. The e.e. values of the two optical active products were determined to be above 99% by HPLC after the formation of two pairs of diastereoisomers with (R)-(+)-α-methylbenzylamine and (S)-phenylalanine methyl ester.

Key words: Methyl hexanoate, 4-t-Butyl 2-n-butylbutane dioic acid, Resolution, e.e. Value

ZHANG Da-tong , TANG Li-da , DUAN Gui-yun , ZHAO Gui-long , XU Wei-ren , MENG Li-juan , WANG Jian-wu . Synthesis, Resolution, and Enantiomeric Purity Assay of 2-n-Butylbutanedioic Acid 4-t-Butyl Esters[J]. Chemical Research in Chinese Universities, 2006, 22(5): 584-588.

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Synthesis, Resolution, and Enantiomeric Purity Assay of 2-n-Butylbutanedioic Acid 4-t-Butyl Esters

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