Potassium → 2-((S)-6-((R)-4-(2,6-Dimethyl-4-(2-(methylsulfonyl)ethoxy)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetic acid

HRID 237700Notes

Reaction equation

HRID 237700 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][S:11]([CH3:13])=[O:12])[CH:5]=[C:4]([CH3:14])[C:3]=1[C:15]1[CH:23]=[CH:22][C:21]([F:24])=[C:20]2[C:16]=1[CH2:17][CH2:18][C@H:19]2[O:25][C:26]1[CH:38]=[CH:37][C:29]2[C@H:30]([CH2:33][C:34]([OH:36])=[O:35])[CH2:31][O:32][C:28]=2[CH:27]=1.[K].[OH:40]OS([O-])=O.[K+]>CO.O.C(#N)C.O>[CH3:14][C:4]1[CH:5]=[C:6]([O:8][CH2:9][CH2:10][S:11]([CH3:13])(=[O:40])=[O:12])[CH:7]=[C:2]([CH3:1])[C:3]=1[C:15]1[CH:23]=[CH:22][C:21]([F:24])=[C:20]2[C:16]=1[CH2:17][CH2:18][C@H:19]2[O:25][C:26]1[CH:38]=[CH:37][C:29]2[C@H:30]([CH2:33][C:34]([OH:36])=[O:35])[CH2:31][O:32][C:28]=2[CH:27]=1

Participants

7

Reactant 3

HCID 5462222Potassium2×HCID 23707502Potassium hydroxy sulfite2×HCID 717389962-((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)acetic acid

Product 1

HCID 717389972-((S)-6-((R)-4-(2,6-Dimethyl-4-(2-(methylsulfonyl)ethoxy)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a solution of 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)acetic acid (70 mg) in methanol (1.5 mL) and water (0.75 mL) is added potassium peroxomonoslufate (Oxone®) (150 mg). The mixture is stirred for 3 hour at room temperature and then potassium peroxomonoslufate (Oxone®) (80 mg) is added. After stirring for 12 hours at room temperature the mixture is partitioned between ethyl acetate and water. The organic phase is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 50:50→0:100). The product thus obtained is dissolved in acetonitrile/water (1:1) and lyophilized to give the title compound. Yield: 7 mg; LC (method 4): tR=1.71 min; Mass spectrum (ESI+): m/z=555 [M+H]+.

Workup

  1. stirringAfter stirring for 12 hours at room temperature the mixture
  2. customis partitioned between ethyl acetate and water
  3. dry with materialThe organic phase is dried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 50:50→0:100)
  6. customThe product thus obtained

Sources & evidence

ORD record
ord-db67fb1385d7498ca93375862bb18a48
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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