Sodium Hydroxide → HCID 14621514, compound

Participants

Reaction Steps

To a solution of (2R,4R,5S)-5-[(Z)-6-methoxycarbonyl-2-hexenyl]-2-methyl-4-phenylcarbamoyloxymethyl-1,3-dioxane (140 mg) in methanol (2 ml) was added 1 ml of 1N aqueous sodium hydroxide and stirred at room temperature for 90 minutes. The reaction mixture was evaporated in vacuo and the residue was neutralized by acetic acid and extracted with ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate. The solvent was evaporated to dryness and the crude product was purified with preparative TLC (ether : dichloromethane=1:1) to give (2R,4R,5S) -5-[(Z)-6-carboxy-2-hexenyl]-2-methyl-4-phenylcarbamoyloxymethyl-1,3-dioxane (115 mg).

Provenance & Evidence