Water → Boc-Ile-Pro-OBzl

Participants

Reaction Steps

While cooling on ice, DCC (1.24 g, 6.0 mmol) and triethylamine (0.70 ml, 4.0 mmol) were added to DMF (10 ml) containing Boc-L-Ile-OH.1/2 H2O (1.39 g, 6.0 mmol), H-D-Pro-OBzl-HCl (956 mg, 4.0 mmol), and HOBt.H2O (613 mg, 4.0 mmol). After stirring for 8 hours, DMF was removed by evaporation, the residue was dissolved in ethyl acetate, and then successively washed with an aqueous 10% citric acid solution, an aqueous 4% sodium bicarbonate solution, and saturated saline. After drying over MgSO4 and concentrating, the resulting oily substance was purified by flash silica gel chromatography (4×30 cm, 1% methanol/chloroform). to obtain the oily title compound (1.63 g, 3.38 mmol, 85% yield). TLC: Rf=(CHCl3/MeOH=9/1)

Provenance & Evidence