Dicyclohexylcarbodiimide → HCID 67441681, compound

Participants

Reaction Steps

To a stirred solution of 74 (117 mg, 0.20 mmol), Boc-L-valine (132 mg, 0.61 mmol) and DMAP (25 mg, 0.20 mmol) in anhydrous DMF (4 ml) under nitrogen was added DCC reagent (251 mg, 1.22 mmol), and the reaction mixture was stirred at rt for 24 h. The reaction mixture was partitioned between AcOEt and a saturated aqueous solution of sodium bicarbonate. After separation, the organic layer was successively washed with a saturated aqueous solution of sodium bicarbonate, a saturated aqueous solution of ammonium chloride and brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by Biotage (Snap 25 g cartridge; MeOH/DCM: 1/99 to 10/90 over 20 CV, then 10/90 over 5 CV), to afford the desired product 74-A (151 mg, 0.195 mmol, 96% yield) as a colorless-white sticky foam. MS (m/z): 776.7 (M+H).

Provenance & Evidence