反应详情

To a solution of 3-[3-(2-Benzoimidazol-1-ylacetyl)phenyl]-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide (67.3 mg, 0.151 mmol; see step (b)) in CH2Cl2 (1 mL) was added BCl3 (0.3 mL, 1.0 M in hexane) and the reaction mixture was stirred for 1 h at ambient temperature. The reaction mixture was concentrated in vacuo. CH2Cl2 (30 mL) was added to the residue and this was washed with water. The organic phase was dried (over anhydrous MgSO4), concentrated in vacuo. To the crude product dissolved in CH2Cl2 (5 mL) was added Na2CO3 (72 mg, 0.680 mmol), water (2 mL) and butyl chloroformate (24.9 μL, 0.196 mmol), and the reaction mixture was stirred for 2 h at ambient temperature. The reaction mixture was diluted with CH2Cl2 (30 mL) and washed with citric acid (10% aq), brine and water, dried (over anhydrous MgSO4), concentrated in vacuo, and the residue purified by flash chromatography using MeOH:CH2Cl2 (6:94) as eluent to give the title compound in 90% yield, over two steps, (66.2 mg, 0.135 mmol).

1. concentrationThe reaction mixture was concentrated in vacuo
2. additionCH2Cl2 (30 mL) was added to the residue
3. washthis was washed with water
4. dry with materialThe organic phase was dried (over anhydrous MgSO4)
5. concentrationconcentrated in vacuo
6. dissolutionTo the crude product dissolved in CH2Cl2 (5 mL)
7. stirringthe reaction mixture was stirred for 2 h at ambient temperature
8. washwashed with citric acid (10% aq), brine and water
9. dry with materialdried (over anhydrous MgSO4)
10. concentrationconcentrated in vacuo
11. customthe residue purified by flash chromatography