Citric Acid → HCID 57120085, compound

Participants

Reaction Conditions

Reaction Steps

16 mg of ethyl (4S,5S)-5-tert-butoxycarbonylamino-4-hydroxy-2-[2-(2-tetrahydropyranyloxy)ethyl]-7-methyl-2-octenoate was dissolved in 0.5 ml of dichloromethane, and 13 μl of boron trifluoride ethyl ether complex was added thereto as -78° C. under stirring. The mixture was stirred for 30 minutes at the same temperature. Then, 75 μl of a 1.5M isobutyl aluminum hydride toluene solution was added to the mixture and further stirred for 45 minutes. 60 μl of a 5M acetic acid dichloromethane solution was added thereto at -78° C., and the reaction solution was raised to room temperature. 10 ml of 10% citric acid aqueous solution was added thereto and extracted with ethyl acetate. The extract was washed sequentially with water and a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 15 mg of (4S,5S)-5-tert-butoxycarbonylamino-1,4-dihydroxy- 2-[2-(2-tetrahydropyranyloxy)ethyl]-7-methyl-2-octene as a colorless oily substance.

Provenance & Evidence