Water → HCID 58726192, compound

Participants

Reaction Steps

While cooling on ice, DCC (8.3 g, 30 mmol) and triethylamine (3.5 ml, 25 mmol) were added to DMF (200 ml) containing Boc-L-Ile-OH.1/2 H2O (24.0 g, 100 mmol), H-D-Pro-OBzl-HCl (19.3 g, 80 mmol), and HOBt.H2O (15.3 g, 100 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 (21.5 g, 51 mmol, 72% yield). TLC: Rf=(CHCl3/MeOH=9/1)

Provenance & Evidence