Dichloromethane → HCID 71619144, compound

Participants

Reaction Steps

Triethylamine (Et3N, 9.6 mL) and methanesulfonyl chloride (5.4 mL, 68.4 mmol) were added to a solution of compound 5 (20.2 g, 23.8 mmol) dissolved in THF (100 mL) and anhydrous CH2Cl2 (200 mL) mixed solvent at 0° C. The reaction mixture was then stirred at room temperature overnight. The reaction was quenched with water and extracted with CH2Cl2. Evaporation through rotary evaporation followed by flash chromatography on silica gel using hexane/EtOAc as the eluent afforded product mesylate 6 (20.8 g, 22.5 mmol, 95% yield) as a colorless oil: 1H NMR (500 MHz, CD3COCD3) δ 4.21 (t, J=7.5 Hz, 2H), 4.11 (s, 6H), 3.48 (t, J=5.0 Hz, 2H), 3.42 (s, 2H), 2.94 (s, 3H), 1.94-1.90 (m, 2H); 13C NMR (126 MHz, CD3COCD3) δ 122.9 (q, J=293.0 Hz), 81.2-81.0 (m), 68.6, 68.5, 67.1, 67.0, 47.7, 37.6, 30.7; 19F NMR (470 MHz, CD3COCD3) δ −71.19 (s); MS (APCI) m/z 927 (M+H)+, 831 (M−OMs)+; HRMS (ESI) calcd for C21H18F27O7S, 927.0342 (M+H)+, 944.0608 [M+NH4]+. found 927.0357, 944.0553, respectively.

Provenance & Evidence