Potassium → methyl 2-((3S)-6-((1R)-4-(2,6-dimethyl-4-(2-(methylsulfinyl)ethoxy)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate

HRID 237449Notes

Reaction equation

HRID 237449 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][S:11][CH3:12])[CH:5]=[C:4]([CH3:13])[C:3]=1[C:14]1[CH:22]=[CH:21][C:20]([F:23])=[C:19]2[C:15]=1[CH2:16][CH2:17][C@H:18]2[O:24][C:25]1[CH:38]=[CH:37][C:28]2[C@H:29]([CH2:32][C:33]([O:35][CH3:36])=[O:34])[CH2:30][O:31][C:27]=2[CH:26]=1.[K].[OH:40]OS([O-])=O.[K+]>CO.O>[CH3:13][C:4]1[CH:5]=[C:6]([O:8][CH2:9][CH2:10][S:11]([CH3:12])=[O:40])[CH:7]=[C:2]([CH3:1])[C:3]=1[C:14]1[CH:22]=[CH:21][C:20]([F:23])=[C:19]2[C:15]=1[CH2:16][CH2:17][C@H:18]2[O:24][C:25]1[CH:38]=[CH:37][C:28]2[C@H:29]([CH2:32][C:33]([O:35][CH3:36])=[O:34])[CH2:30][O:31][C:27]=2[CH:26]=1

Participants

6

Reactant 3

HCID 5462222PotassiumHCID 23707502Potassium hydroxy sulfiteHCID 86697114Methyl 2-((S)-6-((R)-4-(2,6-dimethyl-4-(2-(methylthio)ethoxy)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate

Product 1

HCID 86697370methyl 2-((3S)-6-((1R)-4-(2,6-dimethyl-4-(2-(methylsulfinyl)ethoxy)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 2-((S)-6-((R)-4-(2,6-dimethyl-4-(2-(methylthio)ethoxy)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate (230 mg) in methanol (4 mL) and water (2 mL) is added potassium peroxomonoslufate (Oxone®) (490 mg). The mixture is stirred for 1 hour at room temperature and then partitioned between dichloromethane and water. The organic phase is dried (MgSO4) and concentrated to give the crude product, which is directly in the next step. Yield: 220 mg; LC (method 4): tR=1.79 min; Mass spectrum (ESI+): m/z=553 [M+H]+.

Workup

  1. custompartitioned between dichloromethane and water
  2. dry with materialThe organic phase is dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2614800c9ef445559924f6e311ba48d9
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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