1,2-Dichloroethane → HCID 69373014, compound

Participants

Reaction Steps

To 2.11 g (5.49 mmol) of the acid from Step F dissolved in anhydrous dichloromethane (100 mL) was added EDC (1.34 g, 7.0 mmol), HOBT (0.95 g, 7.0 mmol), (3S)-3-fluoropyrrolidine hydrochloride (880 mg, 7.0 mmol) and N,N′-diisopropylethylamine (1.1 mL, 7.0 mmol). After stirring for 48 h at room temperature, the reaction mixture was concentrated and diluted with 100 mL of 10% aqueous hydrochloric acid. The resultant mixture was then extracted with three 150-mL portions of ethyl acetate, the organic phases combined and washed sequentially with 5% hydrochloric acid, saturated aqueous sodium bicarbonate solution, and saturated aqueous brine (100 mL each). The organic phase was then dried over magnesium sulfate, filtered, and evaporated in vacuo to yield the crude material as a viscous oil. The crude material was purified by flash chromatography on a Biotage® system (silica gel, 0 to 40% ethyl acetate/hexanes gradient) to give the title compound as a colorless solid. LC/MS 471.3 (M+1).

Provenance & Evidence