Hydrochloric Acid → 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

HRID 237699Notes

Reaction equation

HRID 237699 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][S:13]([CH3:15])=[O:14])[CH:7]=[C:6]([CH3:16])[C:5]=1[C:17]1[CH:25]=[CH:24][C:23]([F:26])=[C:22]2[C:18]=1[CH2:19][CH2:20][C@H:21]2[O:27][C:28]1[CH:41]=[CH:40][C:31]2[C@H:32]([CH2:35][C:36]([O:38]C)=[O:37])[CH2:33][O:34][C:30]=2[CH:29]=1.Cl>CO>[CH3:16][C:6]1[CH:7]=[C:8]([O:10][CH2:11][CH2:12][S:13]([CH3:15])=[O:14])[CH:9]=[C:4]([CH3:3])[C:5]=1[C:17]1[CH:25]=[CH:24][C:23]([F:26])=[C:22]2[C:18]=1[CH2:19][CH2:20][C@H:21]2[O:27][C:28]1[CH:41]=[CH:40][C:31]2[C@H:32]([CH2:35][C:36]([OH:38])=[O:37])[CH2:33][O:34][C:30]=2[CH:29]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 M aqueous NaOH solution (480 μL) is added to a solution of 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 (180 mg) in methanol (5 mL) at room temperature. The mixture is stirred at room temperature for 12 hours. The mixture is neutralized with 1 M aqueous HCl solution and partitioned between diethylether and brine. The organic phase is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 60:40→10:90) to give the title compound. Yield: 80 mg; LC (method 4): tR=1.71 min; Mass spectrum (ESI+): m/z=539 [M+NH4]+.

Workup

  1. custompartitioned between diethylether and brine
  2. dry with materialThe organic phase is dried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 60:40→10:90)

Sources & evidence

ORD record
ord-d020a74329374b9fbf63dfe2e9444ec4
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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