Citric Acid → HCID 57901776, compound

HRID 1851471Notes

Reaction equation

HRID 1851471 reaction equation
C[O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[S:10]([NH:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:22]=1[NH:21][C:20]([C:23]([O:25]CC)=[O:24])=[CH:19]2)(=[O:12])=[O:11])=[O:4].CO.[OH-].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[S:10]([NH:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:22]=1[NH:21][C:20]([C:23]([OH:25])=[O:24])=[CH:19]2)(=[O:12])=[O:11])([OH:4])=[O:2]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 57901572HCID 57901572, compound

Product 1

HCID 57901776HCID 57901776, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of ethyl 7-({[2-(methoxycarbonyl)-3-thienyl]sulfonyl}amino)-1H-indole-2-carboxylate (0.35 g) in tetrahydrofuran (10 mL)-methanol (10 mL) was added aqueous solution (5 mL) of 85% potassium hydroxide (350 mg), and the mixture was stirred at room temperature for 18 hr. Aqueous citric acid solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained crystals were washed with ethyl acetate-hexane to give the title compound (193 mg, yield 62%) as pale-yellow crystals. melting point 272-275° C. (decomposition).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washThe obtained crystals were washed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-0406d1c3fa69436e9f669b6861c2ee90
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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