Hydrogen Peroxide → HCID 67977242, compound

HRID 1184729Notes

Reaction equation

HRID 1184729 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([CH:13]2[CH2:17][C:16]3[CH:18]=[C:19]([C:22]4[CH:27]=[CH:26][C:25]([S:28][CH3:29])=[CH:24][C:23]=4[CH3:30])[CH:20]=[CH:21][C:15]=3[O:14]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].OO.FC(F)(F)C([OH:40])C(F)(F)F>ClCCl>[CH:1]([O:4][C:5]([N:7]1[CH2:8][CH2:9][CH:10]([CH:13]2[CH2:17][C:16]3[CH:18]=[C:19]([C:22]4[CH:27]=[CH:26][C:25]([S:28]([CH3:29])=[O:40])=[CH:24][C:23]=4[CH3:30])[CH:20]=[CH:21][C:15]=3[O:14]2)[CH2:11][CH2:12]1)=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 135291,1,1,3,3,3-Hexafluoro-2-propanolHCID 67973310HCID 67973310, compound

Product 1

HCID 67977242HCID 67977242, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-[5-(2-methyl-4-methylsulfanyl-phenyl)-2,3-dihydro-benzofuran-2-yl]-piperidine-1-carboxylic acid isopropyl ester (20 mg), aqueous hydrogen peroxide solution (35%; 3.5 μL) and 1,1,1,3,3,3-hexafluoro-2-propanol (200 μL) is stirred at room temperature for 2 h. The reaction mixture is diluted with dichloromethane and extracted with sodium thiosulfate solution (10%; 2 mL). The organic phase is washed with brine, dried over MgSO4 and the solvent is evaporated. The residue is chromatographed on silica gel (dichloromethane/methanol 95:5) to give the title compound. Yield: 9 mg (43% of theory); LC (method 2): tR=1.45 min; Mass spectrum (ESI+): m/z=442 [M+H]+.

Workup

  1. extractionextracted with sodium thiosulfate solution (10%; 2 mL)
  2. washThe organic phase is washed with brine
  3. dry with materialdried over MgSO4
  4. customthe solvent is evaporated
  5. customThe residue is chromatographed on silica gel (dichloromethane/methanol 95:5)

Sources & evidence

ORD record
ord-e35bbd446f4c4f658f085677ea168560
Source dataset
uspto-grants-2014_03
Patent number
US08669271B2

Reaction notes

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