Preparation of 2R, 3S, 2′R-nadolol enantiomer using S-(-)-menthyl chloroformate as a chiral derivatizing reagent

被引：0
|
作者：
Ju-Il Sung
Ngoc Van Thi Nguyen
Min-Jung Park
Seung-Beom Lee
Yong-Jae Lee
Seung-Ho Choi
Kyeong Ho Kim
机构：
[1] Kangwon National University,College of Pharmacy
来源：
Archives of Pharmacal Research | 2010年 / 33卷
关键词：
Diastereomer; Chiral; Derivatizing reagent; Hydrolysis; S-(-)-Menthyl chloroformate;
D O I：
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中图分类号：
学科分类号：
摘要：
Stereoisomers of nadolol were derivatized with S-(-)-menthyl chloroformate((-)-MCF) forming their diastereomers, RSR-nadolol-(-)-MCF, SRS-nadolol-(-)-MCF, RRS-nadolol-(-)-MCF and SSRnadolol-(-)-MCF. Diastereomeric mixture were then chromatographically resolved by preparative HPLC (JAIGEL-ODS-BP-L, 500 × 25 mm column) eluted with methanol-water (84:16, v/v) at flow rate 2.5 mL/min. RSR-nadolol-(-)-MCF diastereomer was hydrolyzed with 5% LiOH at 80°C for 48 h, and the decomposed mixture was further purified by semi-preparative HPLC. The purity and final yield of RSR-nadolol were 99.97% and 12.95%, respectively.
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页码：1301 / 1306
页数：5
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