Triethylamine → (R)-3-[[N-(2-(tert-butoxycarbonylamino)-5-trifluoromethylbenzoyl)glycyl]amino]-1-(4-chlorobenzyl)pyrrolidine

Participants

Reaction Steps

Triethylamine (2.9 mL, 20.5 mmol), 2-(tert-butoxycarbonylamino)-5-(trifluoromethyl)benzoic acid (6.27 g, 20.5 mmol), EDCI (3.9 g, 20.5 mmol) and HOBt (2.8 g, 20.5 mmol) were added to a dichloromethane (100 mL) solution of (R)-1-(4-chlorobenzyl)-3-(glycylamino)pyrrolidine (5.0 g, 18.7 mmol). The resulting reaction mixture was stirred at room temperature overnight. A 2 M aqueous solution (80 mL) of NaOH was added to the reaction mixture, and the resulting mixture was extracted with dichloromethane. The obtained extract was dried over anhydrous Na2SO4, filtered, concentrated and purified by column chromatography [SiO2, hexane/ethyl acetate=(1:1) to (1:4)] to thereby afford (R)-3-[[N-(2-(tert-butoxycarbonylamino)-5-trifluoromethylbenzoyl)glycyl]amino]-1-(4-chlorobenzyl)pyrrolidine (9.41 g, 91%) as a white amorphous solid. ESI/MS m/e 555.2 (M++H, C26H30ClF3N4O4).

Provenance & Evidence