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

HRID 237720Notes

Reaction equation

HRID 237720 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:9]=[C:8]([CH2:10][CH2:11][CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:7]=[C:6]([CH3:17])[C:5]=1[C:18]1[CH:26]=[CH:25][C:24]([F:27])=[C:23]2[C:19]=1[CH2:20][CH2:21][C@H:22]2[O:28][C:29]1[CH:42]=[CH:41][C:32]2[C@H:33]([CH2:36][C:37]([O:39]C)=[O:38])[CH2:34][O:35][C:31]=2[CH:30]=1>CO>[CH3:17][C:6]1[CH:7]=[C:8]([CH2:10][CH2:11][CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:9]=[C:4]([CH3:3])[C:5]=1[C:18]1[CH:26]=[CH:25][C:24]([F:27])=[C:23]2[C:19]=1[CH2:20][CH2:21][C@H:22]2[O:28][C:29]1[CH:42]=[CH:41][C:32]2[C@H:33]([CH2:36][C:37]([OH:39])=[O:38])[CH2:34][O:35][C:31]=2[CH:30]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 86697206Methyl 2-((S)-6-((R)-4-(2,6-dimethyl-4-(3-(methylsulfonyl)propyl)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate

Product 1

HCID 866973892-((S)-6-((R)-4-(2,6-Dimethyl-4-(3-(methylsulfonyl)propyl)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

1 M aqueous NaOH solution (50 μL) is added to a solution of methyl 2-((S)-6-((R)-4-(2,6-dimethyl-4-(3-(methylsulfonyl)propyl)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate (20 mg) in methanol (2 mL). The mixture is stirred at room temperature for 12 hours and at 50° C. for 2 days. 1 M aqueous NaOH solution (18 μL) is added and the mixture is stirred at 50° C. for 2 hours. Methanol is evaporated in vacuo, the residue is diluted with water and neutralized with 1 M aqueous HCl. The resulting mixture is extracted with ethyl acetate, and the organic phase is dried (MgSO4). The solvent is evaporated and the residue is purified by HPLC on reversed phase to give the title compound. Yield: 7 mg; LC (method 8): tR=0.34 min; Mass spectrum (ESI+): m/z=553 [M+H]+.

Workup

  1. stirringthe mixture is stirred at 50° C. for 2 hours
  2. customMethanol is evaporated in vacuo
  3. additionthe residue is diluted with water and neutralized with 1 M aqueous HCl
  4. extractionThe resulting mixture is extracted with ethyl acetate
  5. dry with materialthe organic phase is dried (MgSO4)
  6. customThe solvent is evaporated
  7. customthe residue is purified by HPLC on reversed phase

Sources & evidence

ORD record
ord-0b29ddbfde6f48e48297727ec81f5ea6
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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