EMAIL THIS PAGE TO A FRIEND

Bioscience, biotechnology, and biochemistry

Preparation of optically active 2-aminobutanoic acid via optical resolution by replacing crystallization.


PMID 17485843

Abstract

An attempt was made to use a simple procedure to obtain (R)- and (S)-2-aminobutanoic acids [(R)- and (S)-1] which are non-proteinogenic alpha-amino acids and are useful as chiral reagents in asymmetric syntheses. Compound (RS)-1 p-toluenesulfonate [(RS)-2], which is known to exist as a conglomerate, was optically resolved by replacing crystallization with (R)- and (S)-methionine p-toluenesulfonate [(R)- and (S)-3] as optically active co-solutes. When (S)-3 was employed as the co-solute, (R)-2 was preferentially crystallized from a supersaturated solution of (RS)-2 in 1-propanol, as was (S)-2 in the presence of (R)-3. (R)- and (S)-2 recrystallized from 1-propanol were treated with triethylamine in methanol to give (R)- and (S)-1 in optically pure forms.

Related Materials

Product #

Image

Description

Molecular Formula

Add to Cart

116122
D-2-Aminobutyric acid, 98%
C4H9NO2
162663
DL-2-Aminobutyric acid, ReagentPlus®, 99%
C4H9NO2