Dimethylformamide → HCID 53358940, compound

Participants

Reaction Steps

To a stirred solution of rac-(2R,3S,4R,5S)-3-(3-chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid (61 mg, 0.13 mmol) in N,N-dimethyl formamide (5 mL) was added diisopropylethylamine (126.1 mg, 0.976 mmol), HOBt (35.3 mg, 0.262 mmol), HBTU (97.8 mg, 0.258 mmol) and methyl-trans-4-aminomethyl-cyclohexane carboxylic acid HCl (56.2 mg, 0.256 mmol, AK Scientific). After it was stirred at rt for 2.5 hrs, the solvent was removed and the reaction mixture was extracted with EtOAc and washed with 1N NaOH (2×), water, and saturated NaCl. The organic phase was separated and dried over Na2SO4. The reaction mixture was then purified by flash column to give rac 4-({[(2R,3S,4R,5S)-4-(4-Chloro-2-fluoro-phenyl)-3-(3-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carbonyl]-amino}-methyl)-cyclohexanecarboxylic acid methyl ester (64.0 mg, 79%) and a white solid foam. HRMS (ES+) m/z Calcd C32H37Cl2F2N3O3+H [(M+H): 620.2253. Found: 620.2253.

Provenance & Evidence