Sodium borohydride → HCID 59625452, compound

Participants

Reaction Conditions

Reaction Steps

Calcium chloride (420 mg) was suspended in ethanol (5 ml), and sodium borohydride (286 mg) was added at 0° C. The mixture was stirred at 0° C. for 15 min, and a solution of methyl 3-[(tert-butoxycarbonyl)amino]-N-({2-tert-butyl-4-[(furan-2-ylmethyl)amino]pyrimidin-5-yl}carbonyl)-N-(2-methylpropyl)-L-alaninate (105 mg) in THF (5 ml) was added dropwise. The mixture was stirred at room temperature for 1.5 hr, the reaction mixture was diluted with 10% aqueous citric acid solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to reversed-phase preparative HPLC, and fractions eluted with water-acetonitrile (9:1) to acetonitrile were collected. The mixture was basified (pH 10) with saturated aqueous potassium carbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the object compound (65 mg).

Provenance & Evidence