Potassium hydroxy sulfite → HCID 86607785, compound

HRID 1270391Notes

Reaction equation

HRID 1270391 reaction equation
[OH:1]OS([O-])=O.[K+].[CH3:7][S:8][C:9]1[N:10]=[C:11]([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]([CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:15]2=[O:31])[S:12][CH:13]=1>O.C(O)(C)C.C(Cl)(Cl)Cl>[CH3:7][S:8]([C:9]1[N:10]=[C:11]([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]([CH2:23][C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[C:15]2=[O:31])[S:12][CH:13]=1)=[O:1]

Participants

6

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 58842238HCID 58842238, compound

Product 1

HCID 86607785HCID 86607785, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 6212ChloroformSolvent

Procedure

A solution of OXONE® in water (0.5 mL) was added to a solution of tert-butyl {3-[4-(methylthio)-1,3-thiazol-2-yl]-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}acetate from Step C (110 mg, 0.291 mmol) in isopropanol (1 mL) and chloroform (1 mL) at 0° C. After 2 h, the mixture was quenched with saturated aqueous NaCl and extracted with CHCl3 (2×10 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—90:10 to 50:50, to give the title compound. MS: m/z=394 (M+1).

Workup

  1. customthe mixture was quenched with saturated aqueous NaCl
  2. extractionextracted with CHCl3 (2×10 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with a gradient of hexane

Sources & evidence

ORD record
ord-51b8790fcc4f474e9dc0652ed3081654
Source dataset
uspto-grants-2007_04
Patent number
US07202251B2

Reaction notes

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