4-Methoxybenzenesulfonyl chloride → HCID 19705455, compound

Participants

Reaction Steps

A cold (0° C.) solution of tert-butyl α-(1-aminomethyl)-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetate (337 mg, 0.867 mmol) in dry CH2Cl2 (3 mL) is treated with diisopropylethylamine (240 μL, 1.30 mmol) and 4-methoxybenzenesulfonyl chloride (215 mg, 1.30 mmol). The solution was allowed to slowly warm to room temperature, stirring overnight under N2. After diluting with CH2Cl2 (25 mL), the solution is washed with dilute NaHCO3 (10 mL), H2O (10 mL), and brine (10 mL). The organic layer was dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure to give 460 mg of a yellow oil. The oil was purified by silica gel chromatography (20 g SG; 25% EtOAc/hexane) to provide 383 mg (79%) of the desired material as a white amorphous solid:

Provenance & Evidence