Dichloromethane → HCID 86679428, compound

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 4-methoxy-3-(methylsulfonamido)benzyl(methyl)carbamate (189.1 mg, 0.549 mmol) was dissolved in dry DMF (10 ml) and cooled to 0° C. Nan (60% w/w dispersion in mineral oil, 48.3 mg, 1.208 mmol) was added, and the mixture was stirred 5 minutes at 0° C. and then 5 minutes at RT. 4-(2-Chloroethyl)morpholine hydrochloride (123 mg, 0.659 mmol) was added, and the mixture was stirred at RT for overnight. Additional NaH (43.93 mg, 1.098 mmol) was added over 4 days with stirring at RT. The reaction was quenched with water and brine and extracted with Et2O and twice with EtOAc. The combined organic layers were dried over Na2SO4, and the solvent was evaporated under vacuum. The crude product was purified by silica gel cartridge using as eluent:DCM to DCM/EtOAc 2:8 to give tert-butyl 4-methoxy-3-(N-(2-morpholinoethyl)methylsulfonamido)benzyl(methyl)carbamate (114 mg, 0.249 mmol, 45.4% yield).

Provenance & Evidence