Tetrahydrofuran → [1-(4-methanesulfonyl-2-trifluoromethyl-benzyl)-2-methyl-1H-indol-3-yl]-acetic acid

HRID 1364582Notes

Reaction equation

HRID 1364582 reaction equation
C[O:2][C:3](=[O:30])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][C:16]=2[C:25]([F:28])([F:27])[F:26])[C:6]=1[CH3:29].C1COCC1.[OH-].[Na+]>CO>[CH3:24][S:21]([C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:5]([CH2:4][C:3]([OH:30])=[O:2])=[C:6]2[CH3:29])=[C:16]([C:25]([F:28])([F:27])[F:26])[CH:17]=1)(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66936534[1-(4-methanesulfonyl-2-trifluoromethyl-benzyl)-2-methyl-1H-indol-3-yl]-acetic acid methyl ester

Product 1

HCID 23627404[1-(4-methanesulfonyl-2-trifluoromethyl-benzyl)-2-methyl-1H-indol-3-yl]-acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirring solution of [1-(4-methanesulfonyl-2-trifluoromethyl-benzyl)-2-methyl-1H-indol-3-yl]-acetic acid methyl ester (440 mg, 1.0 mmol) in 1:1 THF:MeOH (20 ml) at room temperature, is added 1N NaOH aq (5 ml). The reaction mixture is stirred at room temperature for 16 h. The reaction mixture is evaporated in vacuo, diluted with water (10 ml) and acidified to acidic pH with 6N HCl aq. The precipitated product is collected by filtration and recrystallised from 1:3 isopropyl alcohol:water. The product is dried under high vacuum at 50° C.; [M+H]+ 426.

Workup

  1. customThe reaction mixture is evaporated in vacuo
  2. additiondiluted with water (10 ml)
  3. filtrationis collected by filtration
  4. customrecrystallised from 1:3 isopropyl alcohol
  5. customThe product is dried under high vacuum at 50° C.

Sources & evidence

ORD record
ord-ab866adcb5e54a08bb31ee34e86464b4
Source dataset
uspto-grants-2011_02
Patent number
US07888383B2

Reaction notes

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