Trifluoroacetic acid → HCID 71190250, compound

Participants

Reaction Steps

To a solution of (1R,4S,5R,9S,10S,12S,13S,14S)-14-(methoxymethoxy)-5,9-dimethyl-13-(methylsulfinyl)tetracyclo[10.2.2.01,10.04,9]hexadecane-5-carboxylic acid (4.1 mg, 0.0099 mmol) obtained in Example 115 in tetrahydrofuran (2 mL) was added trifluoroacetic acid (2 mL) under stirring on ice. After stirring at 50° C. for 29 hours, the reaction mixture was evaporated, to give (1R,4S,5R,9S,10S,12S,13S,14S)-14-hydroxy-5,9-dimethyl-13-(methylsulfinyl)tetracyclo[10.2.2.01,10.04,9]hexadecane-5-carboxylic acid. This product was further purified by silica gel column chromatography so as to separate two isomers based on the configuration of sulfoxide, to give isomer 1 (0.71 mg) and isomer 2 (1.01 mg).

Provenance & Evidence