Compound 9

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InChIKey VQOBOLPUWFTYHM-MRVPVSSYSA-N

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

A solution of HCO₂H (0.35 mL, 9.2 mmol) in CH₃CN (3 mL) was added to a solution of ClSO₂NCO (0.8 mL, 9.2 mmol) in CH₃CN (5 mL) over 10 min and the mixture was stirred at ambient temperature (23 ^oC) for 8 h. A solution of alcohol 8 (1.32 g, 4.6 mmol) in dimethylacetamide (DMA, 6 mL) was then added to the reaction mixture at 0 ^oC and the resulting solution was stirred at 23 ^oC for 2 h. Upon completion of the reaction, it was quenched with water (20 mL) and extracted with Et₂O (50 mL). The separated aqueous layer was extracted with Et₂O (2 x 100 mL) and the combined organic layers were washed with water (5 x 50 mL), dried over MgSO₄, and concentrated. The residue was purified by flash column chromatography (EtOAc/hexane: 20-40%) to give sulfamate 9 (1.4 g, 3.9 mmol, 90% yield) as a colorless solid. ¹H NMR (500 MHz, CDCl₃) δ 5.97 (br s, 1H), 5.74 (s, 2H), 5.51 (dd, J = 8.5, 2.0 Hz, 1H), 3.32 (dd, J = 13.0, 7.0 Hz, 2H), 3.17 (dd, J = 16.5, 2.0 Hz, 1H), 2.92 (dd, J = 16.5, 9.0 Hz, 1H), 2.24 (dt, J = 7.0, 2.5 Hz, 2H), 1.98 (t, J = 2.5 Hz, 1H), 1.69-1.63 (m, 2H), 1.59-1.53 (m, 2H); ¹³C NMR (125 MHz, CDCl₃) δ 169.0, 98.5, 85.9, 84.0, 69.2, 39.7, 38.2, 28.4, 25.6, 18.1; HRMS (ESI+): m/z calcd. for C₁₀H₁₆Cl₃N₂O₄S [M+H] 364.9896, found 364.9890.