Sodium hydride → HCID 89824458, compound

Participants

Reaction Steps

168.5 mg (0.67 mmol) of tert.-butyl-[(2S)-1-hydroxy-3-phenylpropane-2-yl]carbamate were added to 4.9 ml of DMF under argon and mixed with 53.6 mg (1.3 mmol) of sodium hydride (as 60% dispersion in liquid paraffin) at a temperature of 0° C. After 30 minutes 200 mg (0.74 mmol) of tert.-butyl-4-(brommethyl)benzoate was added at a temperature of 0° C. Following completion of measuring, the batch was stirred for 2 hours at RT. Afterwards, the batch was evaporated in the rotation steam boiler, the residue absorbed in ice water and the compound extracted with 50 ml of dichlormethane each. The organic phases were washed in saturated sodium hydride solution, dried over magnesium sulphate and evaporated in a vacuum. The raw product thus obtained is being purified by means of preparative HPLC. 50.2 mg (17% o. th.) of the intermediate of tert.-butyl-4-[({(2S)-2-[(tert.-butoxycarbonyl)amino]-3-phenylpropyl}oxy)methyl]benzoate were obtained.

Provenance & Evidence