Benzyl Alcohol → HCID 137194537, compound

Participants

Reaction Steps

A solution of chlorosulfonyl isocyante (25 mL, 0.281 mmol) in dichloromethane, was treated with benzyl alcohol (29 μL, 0.281 mmol) dropwise at room temp, stirred for 30 min, treated with a solution of example 71 (103 mg, 0.234 mmol) and triethylamine (130 μL, 0.936 mmol) in 3 mL of dichloromethane, stirred for 2 h, diluted with 10 mL of dichloromethane and 10 mL of 1N HCl. The organic phase was dried over Na2SO4, concentrated, and purified by silica gel chromatography with a gradient of methanol in dichloromethane (0-3%) to afford the desired product (26 mg, 17% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.59 m, 2 H) 0.68 m, 6 H) 0.91 m, 2 H) 2.01 m, 2 H) 2.18 (m, 2 H) 5.11 (s, 2 H) 7.50 m, 11 H) 8.17 (d, J=7.72 Hz, 1 H) 10.04 (s, 1 H) 11.10 (s, 1 H) 12.13 (s, 1 H) 13.74 (d, J=21.69 Hz, 1 H); (ESI+) m/z 653 (M+H)+ (ESI+) m/z 670 (M+NH4)+ (ESI+) m/z 675 (M+Na)+ (ESI+) m/z 1327 (2M+Na)+ (ESI−) m/z 1303 (2M−H)− (ESI−) m/z 651 (M−H)−.

Provenance & Evidence