Ethyl Acetate → HCID 70663560, compound

HRID 878291Notes

Reaction equation

HRID 878291 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N:14]([CH3:32])[C:15](=[O:31])[C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18](SC3COC3)[CH:17]=2)=[C:4]([O:33][CH3:34])[CH:3]=1.O[O:36][S:37]([O-:39])=O.[K+].[O-]S([O-])(=S)=O.[Na+].[Na+].C[CH2:49][O:50][C:51]([CH3:53])=O>CO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N:14]([CH3:32])[C:15](=[O:31])[C:16]2[CH:21]=[C:20]([C:22]([F:24])([F:23])[F:25])[CH:19]=[C:18]([S:37]([CH:53]3[CH2:49][O:50][CH2:51]3)(=[O:39])=[O:36])[CH:17]=2)=[C:4]([O:33][CH3:34])[CH:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24477Sodium ThiosulfateHCID 23707502Potassium hydroxy sulfiteHCID 70663234HCID 70663234, compound

Product 1

HCID 70663560HCID 70663560, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To an ice-cold solution of N-(4-(4-fluoro-2-methoxyphenyl)pyridin-3-yl)-N-methyl-3-(oxetan-3-ylthio)-5-(trifluoromethyl)benzamide (0.042 g, 85.3 μmol, example 251) in MeOH (2 mL) and water (0.5 mL) was added Oxone® (131 mg, 213 μmol) and the reaction mixture was stirred at room temperature for 2.75 hours. The reaction mixture was poured on 10% aqueous Na2S2O3 solution and EtOAc and the layers were separated. The aqueous layer was extracted twice with EtOAc. The organic layers were washed once with brine, dried over MgSO4, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 5 g column using an MPLC (ISCO) system eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Colorless gum (0.021 g; 46%). MS (ESI): m/z=525.11 [M+H]+.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted twice with EtOAc
  3. washThe organic layers were washed once with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. additiontreated with silica gel
  7. customevaporated
  8. customThe compound was purified by silica gel chromatography on a 5 g column
  9. washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:100)

Sources & evidence

ORD record
ord-a3445d7eca5149d3a587456a36eac988
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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