Ethyl Acetate → HCID 70663412, compound

HRID 878252Notes

Reaction equation

HRID 878252 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]([CH3:31])[C:15](=[O:30])[C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18](SCCO)[CH:17]=2)=[C:4]([O:32][CH3:33])[CH:3]=1.O[O:35][S:36]([O-:38])=O.[K+].[NH4+].[Cl-].[CH3:42][CH2:43][O:44]C(C)=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]([CH3:31])[C:15](=[O:30])[C:16]2[CH:21]=[C:20]([C:22]([F:23])([F:25])[F:24])[CH:19]=[C:18]([S:36]([CH2:42][CH2:43][OH:44])(=[O:38])=[O:35])[CH:17]=2)=[C:4]([O:32][CH3:33])[CH:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 23707502Potassium hydroxy sulfiteHCID 70663250HCID 70663250, compound

Product 1

HCID 70663412HCID 70663412, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To an ice-cold solution of N-[4-(4-fluoro-2-methoxy-phenyl)-pyridin-3-yl]-3-(2-hydroxy-ethylsulfanyl)-N-methyl-5-trifluoromethyl-benzamide (0.1 g, 208 μmol, example 216) in MeOH (4 mL) and water (0.5 mL) was added Oxone® (320 mg, 520 μmol) and the white suspension was stirred at room temperature for 3.25 hours. The white suspension was poured on saturated aqueous NH4Cl solution and EtOAc. The two layers were separated and the aqueous layer was extracted twice with EtOAc. The organic layers were washed once with aqueous sodium thiosulfate 10% solution and 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 foam (0.069 g; 64%). MS (ESI): m/z=513.11 [M+H]+.

Workup

  1. customThe two layers were separated
  2. extractionthe aqueous layer was extracted twice with EtOAc
  3. washThe organic layers were washed once with aqueous sodium thiosulfate 10% solution and 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-85c83c2a9dbd41feac89b10e580126cc
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

Loading…