Lithium Hydroxide → [5-fluoro-(4-methanesulfonyl-2-trifluoromethyl-benzyl)-2-methyl-1H-indol-3-yl]-acetic acid

HRID 1364584Notes

Reaction equation

HRID 1364584 reaction equation
C([O:3][C:4](=[O:32])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([F:15])[CH:13]=2)[N:8]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][C:18]=2[C:27]([F:30])([F:29])[F:28])[C:7]=1[CH3:31])C.[Li+].[OH-]>C1COCC1>[F:15][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:24])=[O:25])=[CH:19][C:18]=1[C:27]([F:28])([F:29])[F:30])[C:7]([CH3:31])=[C:6]2[CH2:5][C:4]([OH:32])=[O:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66936503[5-fluoro-(4-methanesulfonyl-2-trifluoromethyl-benzyl)-2-methyl-1H-indol-3-yl]-acetic acid ethyl ester

Product 1

HCID 23627405[5-fluoro-(4-methanesulfonyl-2-trifluoromethyl-benzyl)-2-methyl-1H-indol-3-yl]-acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of [5-fluoro-(4-methanesulfonyl-2-trifluoromethyl-benzyl)-2-methyl-1H-indol-3-yl]-acetic acid ethyl ester (28 mg, 0.06 mmol) dissolved in THF (1 ml) at room temperature, is added 2N LiOH aq (1 ml). The reaction mixture is stirred at room temperature for 2 h and partitioned between water/EtOAc (20 ml). The aqueous phase is separated and acidified with 1N HCl aq to pH 4. The product is extracted into EtOAc (20 ml), dried (MgSO4) and evaporated in vacuo; [M+H]+ 444.

Workup

  1. custompartitioned between water/EtOAc (20 ml)
  2. customThe aqueous phase is separated
  3. extractionThe product is extracted into EtOAc (20 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-8978a4a94ce04513ae392f56cf854f9e
Source dataset
uspto-grants-2011_02
Patent number
US07888383B2

Reaction notes

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