Methanol → [3-(5-benzenesulfonyl-1-methyl-1H-imidazol-4-ylmethyl)-5-fluoro-2-methyl-indol-1-yl]acetic acid

HRID 1944498Notes

Reaction equation

HRID 1944498 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[C:7]([CH2:15][C:16]2[N:17]=[CH:18][N:19]([CH3:30])[C:20]=2[S:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:23])=[O:22])=[C:6]1[CH3:31].CO.[OH-].[Na+]>O1CCCC1>[C:24]1([S:21]([C:20]2[N:19]([CH3:30])[CH:18]=[N:17][C:16]=2[CH2:15][C:7]2[C:8]3[C:13](=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=3)[N:5]([CH2:4][C:3]([OH:32])=[O:2])[C:6]=2[CH3:31])(=[O:23])=[O:22])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium Hydroxide2×HCID 67045042[3-(5-benzenesulfonyl-1-methyl-1H-imidazol-4-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acid methyl ester

Product 1

HCID 58201236[3-(5-benzenesulfonyl-1-methyl-1H-imidazol-4-ylmethyl)-5-fluoro-2-methyl-indol-1-yl]acetic acidYield 91.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [3-(5-benzenesulfonyl-1-methyl-1H-imidazol-4-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acid methyl ester (0.027 g), methanol (3.0 mL) and 1.0 M aqueous sodium hydroxide solution (0.12 mL) was stirred at room temperature for 1 hour. The mixture was treated with tetrahydrofuran (1.0 mL) and 1.0 M aqueous sodium hydroxide solution (0.24 mL), and stirred at room temperature for 4 hours and then at 40° C. for 30 minutes. The mixture was concentrated under reduced pressure and acidified by the addition of 1.0 M aqueous hydrochloric acid solution. The resulting precipitate was collected by filtration, washed with water and dried to afford the title compound as a white solid (0.024 g).

Workup

  1. stirringstirred at room temperature for 4 hours
  2. waitat 40° C. for 30 minutes
  3. concentrationThe mixture was concentrated under reduced pressure
  4. additionacidified by the addition of 1.0 M aqueous hydrochloric acid solution
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-9c7ddff6ae5e4b4fa66246c93dcdb712
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

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