Potassium Carbonate → HCID 59552179, compound

Participants

Reaction Steps

To a stirred solution of (S,Z)-5-((2R,3R,5S,6S)-2,5-dimethyl-6-((E)-3-methylpenta-2,4-dienyl)-tetrahydro-2H-pyran-3-ylamino)-5-oxopent-3-en-2-yl acetate (26.5 mg, 0.0758 mmol) in MeOH (380 μL) was added K2CO3 (26.3 mg, 0.190 mmol) at 0° C. under an open atmosphere. After 2 h at the same temperature the reaction was diluted with saturated aqueous NH4Cl (60 μL) and stirred for 5 min. The resulting reaction mixture was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The resulting residue was purified by flash chromatography (20→50% EtOAc in hexanes) on silica gel (3 mL) to give (S,Z)-N-((2R,3R,5S,6S)-2,5-dimethyl-6-((E)-3-methylpenta-2,4-dienyl)-tetrahydro-2H-pyran-3-yl)-4-hydroxypent-2-enamide (19.2 mg, 82%) as a colorless oil.

Provenance & Evidence