Hydrochloric Acid → HCID 86654487, compound

Participants

Reaction Conditions

Reaction Steps

YHJ-7-52: (±)-N-(6-Aminohexanoyl)-trans-3-(4-phenoxybenzene-sulfonamido)-4-mercaptopyrrolidine Hydrochloride. To a stirred solution of 1.5 M HCl in ethyl acetate (1 mL) was added (±)-N-Boc-trans-3-(4-phenoxybenzenesulfonamido)-4-tert-butylmercaptopyrrolidine (200 mg, 0.39 mmol) and stirring was continued at room temperature until no starting material was detected by TLC (50% ethyl acetate in hexane). The solvent was evaporated under reduced pressure and the residue was dissolved in CH2Cl2. The solution was cooled to 0° C. and triethylamine (60 μL, 0.43 mmol), HOBt.H2O (54 mg, 0.40 mmol), 6-(tert-butoxycarbonylamino)hexanoic acid (90 mg, 0.39 mmol) and DCC (80 mg, 0.39 mmol) were added. The mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure and the residue was dissolved in ethyl acetate (10 mL) and the organic layer was washed with 10% citric acid and sat. aq NaHCO3, then it was dried over Na2SO4 and evaporated. The residue was purified by flash chromatography (50% ethyl acetate in hexane) to give (±)-N-(6-(tert-butoxycarbonylamino)hexanoyl)-trans-3-(4-phenoxybenzenesulfonamido)-4-tert-butylmercaptopyrrolidine (201 mg, 84%): 1H NMR (300 MHz, CDCl3) δ 7.82 (dd, J=9, 3, 2H), 7.43 (t, J=8, 2H), 7.24 (t, J=7, 1H), 7.08 (m, 4H), 5.13 (br m, 1H, NH), 4.57 (br s, 1H, NH), 3.72-4.10 (m, 2H), 3.00-3.45 (m, 6H), 2.21 (t, J=7, 2H), 1.64 (m, 2H), 1.48 (m, 2H), 1.44 (s, 9H), 1.36 & 1.30 (s, 9H), 1.26 (m, 2H); HRMS (ESI) calculated for C31H45N3O6S2Na+ 642.2642. found 642.2654.

Provenance & Evidence