Methyl iodide → HCID 86654482, compound

Participants

Reaction Conditions

Reaction Steps

(±)-N-Carbamoyl-trans-3-(N-methyl-4-phenoxybenzenesulfonamido)-4-mercaptopyrrolidine. To a solution of (±)-N-Boc-trans-3-(4-phenoxybenzenesulfonamido)-4-tert-butylmercaptopyrrolidine (236 mg, 0.466 mmol) in DMF (2 mL) at 0° C. was added tBuOK (0.69 mmol). The mixture was stirred at 0° C. for 10 min, then MeI (0.69 mmol) was added. The solution was stirred at 0° C. until TLC analysis showed no starting material remained. Ethyl acetate (20 mL) was added and the solution was extracted with water, then was dried over Na2SO4 and filtered. The solvent was evaporated and the residue was purified by flash chromatography (ethyl acetate) to give (±)-N-Boc-trans-3-(N-methyl-4-phenoxybenzenesulfonamido)-4-tertbutylmercaptopyrrolidine as a white powder (240 mg, 99%): 1H NMR (300 MHz, CD3OD) δ 7.84 (d, J=8, 2H), 7.44 (t, J=8, 2H), 7.24 (t, J=8, 1H), 7.10 (m, 2H), 7.09 (d, J=9, 2H), 4.22 (m, 1H), 3.90 (m, 1H), 3.37 (m, 2H), 3.08 (m, 2H) 2.86 (s, 3H), 1.44 (s, 9H), 1.28 (s, 9H); MS (ESI) m/e 520.2 (M+); HRMS (ESI) calculated for C26H36N2O5S2Na+ 543.1950. found 543.1950.

Provenance & Evidence