Triethylamine → HCID 86635425, compound

Participants

Reaction Steps

To acetic acid 2-[4-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-piperidin-4-yl]-ethyl ester hydrochloride (Ex. 1c, 370 mg, 0.83 mmol) in 8 mL of dichloromethane was added triethylamine (293 mg, 2.9 mmol). After stirring for 5 min, 5-chlorosulfonyl-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester (296 mg, 1.25 mmol) was added in 3 portions. The reaction mixture was stirred for 3 h at room temperature, and then diluted with Ethyl acetate (40 mL), washed with water (50 mL), 0.5 N HCl (2×30 mL) and water (50 mL), dried over Na2SO4, and concentrated under reduced pressure. The crude product was chromatographed with 5-30% Ethyl acetate/hexanes to afford 5-[4-(2-acetoxy-ethyl)-4-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-piperidine-1-sulfonyl]-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester as a clear oil (420 mg, 83%). ESI/CI-MS m/z 609 ([M+H]+).

Provenance & Evidence