Lithium Hydroxide → HCID 68245745, compound

HRID 2409371Notes

Reaction equation

HRID 2409371 reaction equation
C[O:2][C:3]([C:5]1[NH:6][CH:7]=[C:8]([C:10]2[CH:15]=[C:14]([C:16](=[O:24])[NH:17][C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[CH:13]=[CH:12][C:11]=2[CH:25]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH3:26])[CH:9]=1)=[O:4].[Li+].[OH-]>C1COCC1.CO.C([O-])(O)=O.[Na+]>[C:31]([O:30][C:28]([NH:27][CH:25]([C:11]1[CH:12]=[CH:13][C:14]([C:16](=[O:24])[NH:17][C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:15][C:10]=1[C:8]1[CH:9]=[C:5]([C:3]([OH:4])=[O:2])[NH:6][CH:7]=1)[CH3:26])=[O:29])([CH3:32])([CH3:33])[CH3:34]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 71115408HCID 71115408, compound

Product 1

HCID 68245745HCID 68245745, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 4-[2-(1-tert-Butoxycarbonylamino-ethyl)-5-(pyridin-4-ylcarbamoyl)-phenyl]-1H-pyrrole-2-carboxylic acid methyl ester (661 μmol) in THF (1.6 ml) and MeOH (1.6 ml) was added a 1N LiOH solution (1.6 ml). The reaction mixture was stirred at 40° C. for 1.5 hours. The reaction mixture was diluted with saturated NaHCO3 and extracted with EtOAc. The aqueous layer is acidified with a 20% citric acid solution and extracted again with EtOAc. The combined organic layers were dried over MgSO4 and the solvent was removed under reduced pressure.

Workup

  1. extractionextracted with EtOAc
  2. extractionextracted again with EtOAc
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-7fe8141eb5c445cf9b93c72d51986dc3
Source dataset
uspto-grants-2014_08
Patent number
US08815873B2

Reaction notes

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