Sodium Carbonate → N-Butyloxycarbonyl-3-[3-(2-phenylimidazol-1-ylmethyl)phenyl]-5-iso-butyl-thiophene-2-sulfonamide

To a solution of 3-[3-(2-phenylimidazol-1-ylmethyl)phenyl]-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide (31.2 mg, 0.0615 mmol; see step (a)) in CH2Cl2 (1 mL) was added BCl3 (0.2 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. Water (5 mL) was added to the residue and this was then extracted with EtOAc. The combined organic phase was washed with water and brine, dried (over anhydrous MgSO4) and concentrated in vacuo. To the crude product dissolved in CH2Cl2 (5 mL) was added Na2CO3 (29.3 mg, 0.277 mmol), water (2 mL) and butyl chloroformate (15.6 μL, 0.123 mmol), and the reaction mixture was stirred for 11 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 (5:95) as eluent to give the title compound as a white solid in 87% yield, over two steps, (29.4 mg, 0.0533 mmol).

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

ORDレコード

ord-0a6feaffbb194e1eb1573b76306f42b5

出典データセット

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08080571B2