2,4-Dichlorobenzoic Acid → HCID 57798315, compound

Participants

Reaction Steps

A solution of tert-butyl 3-[(1S)-1-aminoethyl]-3-pyridin-2-ylazetidine-1-carboxylate (I-3, 1.35 g, 5.1 mmol) in CH2Cl2 (11 mL) was treated with 2,4-dichlorobenzoic acid (1.2 g, 6.1 mmol) EDCI (2.0 g, 10.2 mmol), and HOBt (690 mg, 5.1 mmol) and stirred at room temperature. After 18 h, the reaction was quenched with the addition of H2O (50 mL) and extracted with CH2Cl2 (3×50 mL). The combined organic extracts were dried (Na2SO4), concentrated under reduced pressure, and purified by flash chromatography (120 g SiO2, 50-80% EtOAc/hexanes) to afford tert-butyl 3-{(1S)-1-[(2,4-dichlorobenzoyl)amino]ethyl}-3-pyridin-2-ylazetidine-1-carboxylate (I-4). Analytical LCMS: single peak (214 nm), 3.010 min. This material was used in subsequent reactions without further purification.

Provenance & Evidence