Acetic Acid → HCID 178464122, compound

Participants

Reaction Steps

To a solution of Example 47 (25 mg, 44 μmol) in 1,2-dichloroethane (2.7 mL) was added acetaldehyde (28 μL, 492 μmol) and acetic acid (8 μL, 96 μmol). The resulting mixture was stirred for 20 min, then sodium triacetoxyborohydride (31 mg, 144 μmol) was added. After stirring for 2 h, the mixture was diluted with EtOAc and washed sequentially with saturated aqueous NaHCO3, water, and brine. The organic phase was dried over Na2SO4, filtered, and the solvent was removed in vacuo. The residue was purified by preparative TLC (90:10:1 CHCl3/MeOH/NH4OH). After concentrating the material in vacuo, the resulting oil was dissolved in CH3CN/H2O/TFA and lyophilized to provide the title compound (8.5 mg, 26%) as a white solid and mixture of diastereomers: ESI MS m/z 577 [C29H35F3N4O3S+H]+.

Provenance & Evidence