Citric Acid → HCID 57901861, compound

HRID 1851483Notes

Reaction equation

HRID 1851483 reaction equation
[CH2:1]([S:4]([C:7]1[CH:15]=[CH:14][C:13]([NH:16][S:17]([C:20]2[S:21][CH:22]=[CH:23][CH:24]=2)(=[O:19])=[O:18])=[C:12]2[C:8]=1[CH:9]=[C:10]([C:25]([O:27]CC)=[O:26])[NH:11]2)(=[O:6])=[O:5])[CH2:2][CH3:3].CO.[OH-].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[CH2:1]([S:4]([C:7]1[CH:15]=[CH:14][C:13]([NH:16][S:17]([C:20]2[S:21][CH:22]=[CH:23][CH:24]=2)(=[O:19])=[O:18])=[C:12]2[C:8]=1[CH:9]=[C:10]([C:25]([OH:27])=[O:26])[NH:11]2)(=[O:5])=[O:6])[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 57901632HCID 57901632, compound

Product 1

HCID 57901861HCID 57901861, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of ethyl 4-(propylsulfonyl)-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxylate (0.56 g) in tetrahydrofuran (15 mL)-methanol (15 mL) was added aqueous solution (5 mL) of 85% potassium hydroxide (0.35 g), and the mixture was stirred at room temperature for 15 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 oil was crystallized from ethyl acetate-hexane to give the title compound (486 mg, yield 93%) as pale-yellow prism crystals. melting point 247-248° C.

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. customThe obtained oil was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-9b61f12707cd400bb1de7502a70a95c5
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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