Water → HCID 66704595, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 2-((3-aminopropyl)(3-chlorophenyl)amino)ethyl(methyl)carbamate (300 mg, 0.88 mmol) in dry CH2Cl2 (5 mL), Et3N (583 mg, 5.3 mmol) was added. The resulting mixture was cooled to 0-5° C. and a solution of methyl chloroformate (965 mg, 10.3 mmol, 5 eq) in dry CH2Cl2 (5 mL) was added dropwise. After addition, the reaction mixture was stirred for 1-2 h at 0-5° C. Upon completion of the reaction, water (10 mL) was added, the aqueous layer was extracted with CH2Cl2 (3×8 mL), the combined organic layers were washed with 10% citric acid (2×5 mL) and brine, then dried over Na2SO4. The filtrate was concentrated to the crude product which was purified by preparative HPLC to tert-butyl 2-((3-(methoxycarbonylamino)propyl)(3-chlorophenyl)amino)ethyl(methyl)carbamate (200 mg, yield 83%).

Provenance & Evidence