Benzyl Alcohol → HCID 137194538, compound

Participants

Reaction Steps

A solution of chlorosulfonyl isocyanate (60 μL, 0.6 mmol) in 4 mL anhydrous dichloromethane at room temperature was treated drop wise with benzyl alcohol (60 μL, 0.6 mmol). After one hour, a solution of Example 34B (238 mg, 0.5 mmol), triethyl amine (300 μL, 2 mmol) in 2 mL dichloromethane, was added drop wise. The reaction was diluted with dichloromethane and extracted with 1 N HCl. The aqueous layer was extracted with dichloromethane and the combined organic layers dried with anhydrous MgSO4, concentrated and purified by chromatography to give the desired product (225 mg, 69%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.42 m, 1 H) 0.69 (d, J=6.62 Hz, 3 H) 0.72 (d, J=6.62 Hz, 3 H) 0.81 m, 1 H) 1.32 m, 1 H) 1.58 (s, 3 H) 2.08 m, 1 H) 2.23 m, 1 H) 5.11 (s, 2 H) 7.30 m, 6 H) 7.47 (dd, J=9.01, 2.39 Hz, 1 H) 7.54 m, 1 H) 7.62 (d, J=2.57 Hz, 1 H) 7.70 (d, J=9.19 Hz, 1H) 7.77 (d, J=3.68 Hz, 2 H) 8.17 (d, J=8.09 Hz, 1 H) 11.12 (s, 1 H) 12.15 (s, 1H) 13.78 (s, 1H). MS (ESI−) m/z=651 (M−H)−.

Provenance & Evidence