Methanol → HCID 70663440, compound

HRID 878259Notes

Reaction equation

HRID 878259 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]([CH3:34])[C:15]([C:17]2[CH:18]=[C:19](SCCC(OC)=O)[CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:22]=2)=[O:16])=[C:4]([O:35][CH3:36])[CH:3]=1.O[O:38][S:39]([O-:41])=O.[K+].[NH4+].[Cl-].C[CH2:46][O:47][C:48]([CH3:50])=[O:49].[CH3:51]O>O>[CH3:46][O:47][C:48](=[O:49])[CH2:50][CH2:51][S:39]([C:19]1[CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:22]=[C:17]([C:15](=[O:16])[N:14]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][C:8]=2[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=2[O:35][CH3:36])[CH3:34])[CH:18]=1)(=[O:41])=[O:38]

Participants

7

Reactant 5

HCID 887MethanolHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 23707502Potassium hydroxy sulfiteHCID 70663482HCID 70663482, compound

Product 1

HCID 70663440HCID 70663440, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of methyl 3-(3-((4-(4-fluoro-2-methoxyphenyl)pyridin-3-yl)(methyl)-carbamoyl)-5-(trifluoromethyl)phenylthio)propanoate (0.2 g, 383 μmol, Example 225) in MeOH (6 mL) and water (0.5 mL) at 0° C. was added Oxone® (588 mg, 957 μmol) and the colorless mixture was stirred at room temperature for 1.75 hours. The white suspension was poured on saturated aqueous NH4Cl solution and EtOAc. The two layers were separated. The aqueous layer was extracted twice with EtOAc. The organic layers were washed with 10% aqueous sodium thiosulfate 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 10 g column using an MPLC (ISCO) system eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Colorless foam (0.165 g; 77%). MS (ESI): m/z=555.12 [M+H]+.

Workup

  1. customThe two layers were separated
  2. extractionThe aqueous layer was extracted twice with EtOAc
  3. washThe organic layers were washed with 10% aqueous sodium thiosulfate 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 10 g column
  9. washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:100)

Sources & evidence

ORD record
ord-6d5629cfd70a43cc85993d25ae2496a0
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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