Toluene → HCID 86604720, compound

Participants

Reaction Conditions

Reaction Steps

A toluene solution of sulfamoyl chloride (1 ml, 0.69 mmol) was evaporated to dryness, cooled to 0° C. and then treated with dimethylacetamide (1.5 mL) then diol 48 (45 mg). After 3 h stirring at rt the reaction was diluted in ethyl acetate (20 mL), then treated with water (10 ml), the organic layer was separated and extracted with brine (5×10 mL), dried and evaporated to give a yellow oil. Column chromatography (gradient 5-10% methanol in chloroform) was used to purify the desired bis-sulfamate 49 as a clear colourless oil (21 mg) which showed δH (CDCl3, TMS=0) 7.03 (1H, s, ArH), 6.90 (1H, s, ArH), 5.02 (4H, br, 2×NH2), 4.37-4.42 (2H, m, CH2OS), 3.87 (3H, s, OMe), 3.75-3.82 (2H, m, OCH2), 3.48 (1H, dd, J 8.6 & 7.9, OCH), 2.74-2.85 (2H, m, 6-CH2), 1.25-2.50 (H, m) and 0.79 (3H, s, 18-CH3); m/z 504.6.

Provenance & Evidence