Lithium Hydroxide → HCID 68245745, compound

HRID 1403672Notes

Reaction equation

HRID 1403672 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-87381486007748bfbcd0ebddc1d90a69
Source dataset
uspto-grants-2014_12
Patent number
US08912209B2

Reaction notes

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