Citric Acid → (2-{5-(2-methoxyethoxy)-7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetic acid

HRID 1960531Notes

Reaction equation

HRID 1960531 reaction equation
C([O:3][C:4](=[O:35])[CH2:5][CH:6]1[S:10][C:9]([C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([O:20][CH2:21][CH2:22][O:23][CH3:24])=[CH:15][C:14]=3[N:25]([CH3:34])[S:26]([C:29]2[S:30][CH:31]=[CH:32][CH:33]=2)(=[O:28])=[O:27])=[N:8][CH2:7]1)C.[OH-].[Na+].O1CCCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[CH3:24][O:23][CH2:22][CH2:21][O:20][C:16]1[CH:17]=[C:18]2[C:13](=[C:14]([N:25]([CH3:34])[S:26]([C:29]3[S:30][CH:31]=[CH:32][CH:33]=3)(=[O:28])=[O:27])[CH:15]=1)[NH:12][C:11]([C:9]1[S:10][CH:6]([CH2:5][C:4]([OH:35])=[O:3])[CH2:7][N:8]=1)=[CH:19]2

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59303535ethyl(2-{5-(2-methoxyethoxy)-7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetate

Product 1

HCID 68460040(2-{5-(2-methoxyethoxy)-7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetic acidYield 98.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl(2-{5-(2-methoxyethoxy)-7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetate (300 mg), 1N aqueous sodium hydroxide solution (2 mL), tetrahydrofuran (2 mL) and ethanol (2 mL) was stirred at room temperature for 15 hr. The reaction mixture was acidified with aqueous citric acid solution, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated to give the title compound (280 mg, yield 97%) as yellow crystals. The crystals were recrystallized from ethyl acetate-hexane to give yellow prism crystals. melting point 113-114° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-787c25f27fdb43ccbf3032a56e687b9a
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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