Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
Enantioseparation by Dual-flow Countercurrent Extraction : Its Application to the Enantioseparation of (±)-Propranolol
Yoshiohiro ABETomoko SHOJIShikie FUKUIMaki SASAMOTOHideyuki NISHIZAWA
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Volume 44 (1996) Issue 8 Pages 1521-1524

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Abstract

Enantioseparation of (±)-propranolol has been demonstrated by countercurrent extraction with a two-phase system composed of a chloroform solution of didodecyl L-tartrate (100mM) and an acetate buffer (50mM, pH 4.4) containing boric acid (100mM). The free base of (±)-propranolol (1.6g) was dissolved in the aqueous phase and extracted five times by means of dual-flow countercurrent extraction. After an additional five extractions for recovery, the crude R-(+)- or S-(-)-form was obtained from the aqueous extracts or organic extracts, respectively. They were isolated as their hydrochloride salts with a purity of 89.8% ee (R-form, 385.7mg) and 88.3% ee (S-form, 429.5mg), respectively. They were purified to over 99% ee by recrystallizing twice from 1-propanol.

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