Lithium Hydroxide → HCID 22144634, compound

HRID 1825004Notes

Reaction equation

HRID 1825004 reaction equation
[CH3:1][C:2]([CH3:33])([CH3:32])[CH2:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]([F:26])([F:25])[F:24])[C:11]([C:27]([O:29]CC)=[O:28])=[CH:10]2)=[O:5].[OH-].[Li+]>CO.C1COCC1>[CH3:1][C:2]([CH3:33])([CH3:32])[CH2:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]([F:24])([F:25])[F:26])[C:11]([C:27]([OH:29])=[O:28])=[CH:10]2)=[O:5]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 22144650Ethyl 5-[(3,3-dimethylbutanoyl)amino]-1-[2-(trifluoromethyl)benzyl]-1H-indole-2-carboxylate

Product 1

HCID 22144634HCID 22144634, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

105 mg (0.26 mmol) of ethyl 5-[(3,3-dimethylbutanoyl)amino]-1-[2-(trifluoromethyl)benzyl]-1H-indole-2-carboxylate from Example LXIII are dissolved in 1 ml each of methanol and THF, and 0.26 ml (0.52 mmol) of 2M lithium hydroxide solution is added. The mixture is heated at 90° C. for one hour. After cooling, the mixture is, for work-up, diluted and extracted with aqueous hydrochloric acid and ethyl acetate. The organic phase is dried with sodium sulphate, filtered and dried under reduced pressure.

Workup

  1. temperatureAfter cooling
  2. additiondiluted
  3. extractionextracted with aqueous hydrochloric acid and ethyl acetate
  4. dry with materialThe organic phase is dried with sodium sulphate
  5. filtrationfiltered
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-828fd79a446a46dd9a43af779ffce061
Source dataset
uspto-grants-2006_05
Patent number
US07045544B2

Reaction notes

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