Tetrahydrofuran → HCID 58459215, compound

HRID 2036558Notes

Reaction equation

HRID 2036558 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]2[N:6]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21](SC)[CH:20]=3)[C:7]([CH:9]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:10])=[N:8][C:4]=2[CH:3]=1.O[O:30][S:31]([O-:33])=O.[K+].[CH2:35]1COCC1>O>[F:1][C:2]1[CH:28]=[CH:27][C:5]2[N:6]([C:19]3[CH:20]=[CH:21][CH:22]=[C:23]([S:31]([CH3:35])(=[O:33])=[O:30])[CH:24]=3)[C:7]([CH:9]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:10])=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 58459228HCID 58459228, compound

Product 1

HCID 58459215HCID 58459215, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of tert-butyl 1-(5-fluoro-1-(3-(methylthio)phenyl)-1H-benzo[d]-imidazol-2-yl)ethylcarbamate (0.7397 g, 1.842 mmol) in THF (13.82 mL) and water (4.61 mL) was added oxone (2.83 g, 4.61 mmol) and the mixture was stirred at rt. After 3 h, water (50 mL) was added to the mixture, and extracted with DCM (50 mL×2). The combined organic layers were dried over Na2SO4, filtered, concentrated under reduced pressure to give a white solid, which was purified by column chromatography on a 24 g of Redi-Sep™ Gold column using 0 to 50% gradient of EtOAc in hexane over 5 min and then 50% isocratic of EtOAC for 20 min as eluent to give tert-butyl 1-(5-fluoro-1-(3-(methylsulfonyl)phenyl)-1H-benzo[d]imidazol-2-yl)ethylcarbamate as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.05-8.15 (2H, m), 7.90 (2H, d, J=4.9 Hz), 7.56 (1H, dd, J=9.5, 2.2 Hz), 7.35 (1H, d, J=8.0 Hz), 7.06-7.18 (2H, m), 4.82-4.95 (1H, m), 3.33 (3H, s), 1.44 (3H, d, J=6.8 Hz), 1.23 (9H, s); LC-MS (ESI) m/z 434.0 [M+H]+.

Workup

  1. extractionextracted with DCM (50 mL×2)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto give a white solid, which
  6. customwas purified by column chromatography on a 24 g of Redi-Sep™ Gold column
  7. customover 5 min

Sources & evidence

ORD record
ord-7325068ce8ba441586b6bd047f23af25
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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