1,2-Dichloroethane → HCID 9873648, compound

Participants

Reaction Conditions

Reaction Steps

N-[(4-Morpholinyl)carbonyl]-L-leucine (100 mg, 0.35 mmol) (prepared as described in Example 1) was dissolved in 10 mL DMF and cooled to 0° C. To the solution was added EDC (77 mg, 0.4 mmol) and HOBt (54 mg, 0.4 mmol) and the reaction was stirred for 1 h. In a separate flask, [1-(2,4-diphenyloxazole-5-carbonyl)-3-phenylpropyl]carbamic acid tert-butyl ester (158 mg, 0.31 mmol) was dissolved in 4 mL CH2Cl2 and 2 mL TFA was added. After stirring for 1 h, the solvents were evaporated, the residue was dissolved in 5 mL DMF and N-methylmorpholine (406 mg, 0.4 mmol) was added. The resulting solution was added to the previously prepared solution of activated leucine derivative at 0° C. The reaction mixture was stirred at room temperature for 3 h, cooled to 0° C., and quenched with 100 mL of a 10% solution of citric acid in water. The resulting mixture was extracted with 3×100 mL EtOAc. The combined organic extracts were washed with 2×100 mL of saturated bicarbonate and 1×100 mL brine. The organic layer was dried over Na2SO4, filtered and concentrated to a residue that was purified by chromatography (florisil, 30%-50% EtOAc in hexane) to give the title compound as a white solid (90 mg, 84%), m.p. 83-5° C., MS (ES) 609 (M+).

Provenance & Evidence