Citric Acid → HCID 57901620, compound

HRID 1851497Notes

Reaction equation

HRID 1851497 reaction equation
[F:1][C:2]1[CH:41]=[CH:40][CH:39]=[CH:38][C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:26]=[C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[F:37])[CH:28]=1)[C:9]([NH:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:20]=1[NH:19][C:18]([C:21]([O:23]CC)=[O:22])=[CH:17]2)=[O:10].CO.[OH-].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[F:37][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[CH2:30][O:29][C:27]1[CH:26]=[C:8]([CH:7]=[C:6]([O:5][CH2:4][C:3]2[CH:38]=[CH:39][CH:40]=[CH:41][C:2]=2[F:1])[CH:28]=1)[C:9]([NH:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:20]=1[NH:19][C:18]([C:21]([OH:23])=[O:22])=[CH:17]2)=[O:10]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 57901655HCID 57901655, compound

Product 1

HCID 57901620HCID 57901620, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of ethyl 7-({3,5-bis[(2-fluorobenzyl)oxy]benzoyl}amino)-1H-indole-2-carboxylate (170 mg) in tetrahydrofuran (8 mL)-methanol (8 mL) was added aqueous solution (5 mL) of 85% potassium hydroxide (150 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 (147 mg, yield 91%) as colorless crystals. melting point 271-273° 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. washThe obtained crystals were washed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-b6ff1fcb5f69486a99954df5baba1620
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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