反应 #2460341

反应方程式

sulfamoyl chloride

NaH

Compound 136

2-(5-Chloro-benzo[b]thiophen-3-yl)-3-hydroxy-N-naphthalen-2-yl-propionamide

sulfamoyl chloride

→

Compound 120

Sulfamic acid 2-(5-chloro-benzo[b]thiophen-3-yl)-2-(naphthalen-2-ylcarbamoyl)-ethyl ester

溶剂

DMF

DMF

反应条件

后处理

1. 1
   workup.STIRRINGAfter stirring for 1 h at 0° C.
2. 2
   workup.STIRRINGAfter stirring overnight
3. 3
   其他quenched with water
4. 4
   萃取extracted with EtOAc (3×5 mL)
5. 5
   洗涤The combined organic phases were washed with brine
6. 6
   干燥dried (Na2SO4)
7. 7
   过滤filtered
8. 8
   浓缩concentrated under reduced pressure at rt
9. 9
   其他The residue was purified by flash column chromatography (silica, 0-40% EtOAc/hexanes)

实验过程

To a suspension of 95% NaH (0.017 g, 0.68 mmol) in DMF (2 mL) at 0° C. was added a solution of Compound 136 (0.10 g, 0.26 mmol) in DMF (2 mL) dropwise. The suspension was stirred at 0° C. for 1 h, then sulfamoyl chloride (0.067 g, 0.58 mmol) was added as a solid. After stirring for 1 h at 0° C., the mixture was treated with excess sulfamoyl chloride. After stirring overnight, the reaction was, quenched with water and extracted with EtOAc (3×5 mL). The combined organic phases were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure at rt. The residue was purified by flash column chromatography (silica, 0-40% EtOAc/hexanes) to yield Compound 120 (0.1.0 g) as a white foam: HPLC: 4.12 min; MS (ES) m/z 461 (MH+); 1H NMR (DMSO-d6) δ 4.29-4.34 (m, 1H), 4.65-4.75 (m, 2H), 7.39-7.50 (m, 3H), 7.57-7.64 (m, 1H), 7.81-7.90 (m, 4H), 8.09 (d, 1H, J=8.5 Hz), 8.215 (d, 1H, J=2 Hz), 8.34 (s, 1H), 10.55 (s, 1H).

来源