反应详情

To a white suspension of 19 (0.075 g, 0.271 mmol) and NEt3 (0.292 mL, 2.71 mmol) in anhydrous CH2Cl2 (2 mL) at 0° C. under an inert atmosphere was added to a colourless solution of N,N-dimethylsulfamoyl chloride (0.408 mL, 3.80 mmol) in anhydrous CHACl2 (3 mL). The resulting white suspension was left to stir under an inert atmosphere at room temperature for 70 h forming a clear orange/brown solution. The reaction mixture was diluted in CH2Cl2 (30 mL) and washed with distilled H2O (30 mL×3) and brine (30 mL). The organic fraction was separated, dried (MgSO4), filtered and solvent removed in vacuo to leave yellow residues. Column chromatography (CH2Cl2/acetone 75:25) eluted 21 as a viscous yellow oil (0.093 g, 90%); 1H NMR δH (270 MHz, CDCl3) 3.00 (s, 6H), 5.44 (s, 2H), 7.28-7.33 (m, 2H), 7.39 (d, J=8.7 Hz, 2H), 7.53 (d, J=8.7 Hz, 2H), 7.76 (d, J=7.9 Hz, 1H), 8.00 (s, 1H) and 8.18 (s, 1H); LCMS (APCI−) m/z (rel intensity) 382 (100, [M−H]+; HRMS (ES+) m/z calcd. for C18H18N5O3S [M+H]+: 384.1125, found 384.1143.

1. waitThe resulting white suspension was left
2. customforming a clear orange/brown solution
3. washwashed with distilled H2O (30 mL×3) and brine (30 mL)
4. customThe organic fraction was separated
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. customsolvent removed in vacuo
8. customto leave yellow residues
9. washColumn chromatography (CH2Cl2/acetone 75:25) eluted 21 as a viscous yellow oil (0.093 g, 90%)