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KMID : 0043320100330091301
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Archives of Pharmacal Research
2010 Volume.33 No. 9 p.1301 ~ p.1306
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Preparation of 2R, 3S, 2′R-nadolol enantiomer using S-(-)-menthyl chloroformate as a chiral derivatizing reagent
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Sung Ju-Il
Nguyen Ngoc Van Thi
Park Min-Jung
Lee Seung-Beom
Lee Yong-Jae
Choi Seung-Ho
Kim Kyeong-Ho
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Abstract
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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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KEYWORD
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Diastereomer, Chiral, Derivatizing reagent, Hydrolysis, S-(-)-Menthyl chloroformate
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