Hydrochloric Acid → HCID 86654484, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1.5 M HCl in ethyl acetate (5 mL) was added (±)-N-Boc-trans-3-(N-methyl-4-phenoxybenzenesulfonamido)-4-tertbutylmercaptopyrrolidine (130 mg, 0.25 mmol) and stirring was continued at room temperature until no starting material was detected by TLC. The solvent was evaporated under reduced pressure and the residue was dissolved in CH2Cl2. The solution was cooled to 0° C. and triethylamine (46 μL, 0.33 mmol) and TMSNCO (100 μL, 0.74 mmol) were added successively. The solution was stirred at room temperature overnight. The reaction mixture was extracted with water and saturated brine, and was dried over Na2SO4 and filtered. The solvent was evaporated and the residue was purified by flash chromatography (5% MeOH in ethyl acetate) to give (±)-N-carbamoyl-trans-3-(N-methyl-4-phenoxybenzenesulfonamido)-4-tert-butylmercaptopyrrolidine as a white powder (110 mg, 95%): 1H NMR (300 MHz, CD3OD) δ 7.85 (m, 2H), 7.42 (m, 2H), 7.22 (m, 1H), 7.10 (m, 4H), 4.24 (m, 1H), 3.96 (m, 1H), 3.42 (m, 2H), 3.08 (m, 2H), 2.87 (s, 3H), 1.28 (s, 9H); MS (ESI) m/e 463.2 (M+); HRMS (ESI) calcd for C22H29N3O4S2Na+ 486.1479. found 486.1481.

Provenance & Evidence