Determination of the Absolute Configuration of the Nabumetone Metabolite 4-(6-Methoxy-2-naphthyl)butan-2-ol Using the Chiral Derivatizing Agent, 1-Fluoroindan-1-carboxylic Acid.

Determination of the Absolute Configuration of the Nabumetone Metabolite 4-(6-Methoxy-2-naphthyl)butan-2-ol Using the Chiral Derivatizing Agent, 1-Fluoroindan-1-carboxylic Acid.
Chem Pharm Bull (Tokyo). 2019;67(1):75-78
Authors: Kamei T, Kimura Y, Koyanagi J, Matsumoto K, Hasegawa T, Akimoto M, Takahashi T
Abstract
The absolute configuration of (+)-4-(6-methoxy-2-naphthyl)butan-2-ol ((+)-MNBO), a nabumetone metabolite, was determined using 1-fluoroindan-1-carboxylic acid (FICA). Both enantiomers of the FICA methyl esters were derivatized to diastereomeric esters of (+)-MNBO by an ester exchange reaction. The results of 1H- and 19F-NMR spectroscopy of the diastereomeric FICA esters of (+)-MNBO confirmed the absolute configuration of (+)-MNBO was (S).
PMID: 30606953 [PubMed - in process]

Source: Chemical and Pharmaceutical Bulletin - January 6, 2019 Category: Drugs & Pharmacology Authors: Kamei T, Kimura Y, Koyanagi J, Matsumoto K, Hasegawa T, Akimoto M, Takahashi T Tags: Chem Pharm Bull (Tokyo) Source Type: research