Enantioseparation by dual-flow countercurrent extraction: Its application to the enantioseparation of (±)-propranolol

Yoshihiro Abe, Tomoko Shoji, Shikie Fukui, Maki Sasamoto, Hideyuki Nishizawa

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

Enantioseparation of (±)-propranolol has been demonstrated by countercurrent extraction with a two-phase system composed of a chloroform solution of didodecyl L-tartrate (100 mM) and an acetate buffer (50 mM, pH 4.4) containing boric acid (100 mM). The free base of (±)-propranolol (1.6 g) 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, 385.7 mg) and 88.3% ee (S-form, 429.5 mg), respectively. They were purified to over 99% ee by recrystallizing twice from 1-propanol.

Original languageEnglish
Pages (from-to)1521-1524
Number of pages4
JournalChemical and Pharmaceutical Bulletin
Volume44
Issue number8
Publication statusPublished - 1996 Aug

Fingerprint

Propranolol
1-Propanol
Chloroform
Buffers
Acetates
Salts
Recovery
tartaric acid
boric acid

Keywords

  • boric acid
  • didodecyl L-tartrate
  • enantioseparation
  • liquid liquid extraction
  • propranolol

ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry
  • Drug Discovery
  • Pharmacology

Cite this

Enantioseparation by dual-flow countercurrent extraction : Its application to the enantioseparation of (±)-propranolol. / Abe, Yoshihiro; Shoji, Tomoko; Fukui, Shikie; Sasamoto, Maki; Nishizawa, Hideyuki.

In: Chemical and Pharmaceutical Bulletin, Vol. 44, No. 8, 08.1996, p. 1521-1524.

Research output: Contribution to journalArticle

Abe, Yoshihiro ; Shoji, Tomoko ; Fukui, Shikie ; Sasamoto, Maki ; Nishizawa, Hideyuki. / Enantioseparation by dual-flow countercurrent extraction : Its application to the enantioseparation of (±)-propranolol. In: Chemical and Pharmaceutical Bulletin. 1996 ; Vol. 44, No. 8. pp. 1521-1524.
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