Lithium Hydroxide → HCID 45255442, compound

HRID 389278Notes

Reaction equation

HRID 389278 reaction equation
C([O:3][C:4](=[O:33])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([C:14]2[C:23]([CH2:24][N:25]([C:28]([CH:30]3[CH2:32][CH2:31]3)=[O:29])[CH2:26][CH3:27])=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)[CH:7]=1)C.[OH-].[Li+]>C1COCC1.O.CCOC(C)=O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH:30]1([C:28]([N:25]([CH2:24][C:23]2[C:14]([C:8]3[CH:7]=[C:6]([CH2:5][C:4]([OH:33])=[O:3])[CH:11]=[CH:10][C:9]=3[O:12][CH3:13])=[N:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:26][CH3:27])=[O:29])[CH2:32][CH2:31]1

Participants

7

Reactant 2

HCID 3939Lithium HydroxideHCID 58579981HCID 58579981, compound

Product 1

HCID 45255442HCID 45255442, compound

Reagents, catalysts & solvents 4

HCID 311Citric AcidSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(3-{3-[(Cyclopropanecarbonyl-ethyl-amino)-methyl]-quinolin-2-yl}-4-methoxy-phenyl)-acetic acid ethyl ester (0.272 g, 0.61 mmol) in THF (5 mL) and H2O (2 mL) was treated with lithium hydroxide (0.090 g, 2.1 mmol) and stirred at room temperature until no starting material was seen by analytical LCMS. The mixture was diluted with EtOAc and H2O, and citric acid was added to acidify the solution. The mixture was extracted with EtOAc, and the combined organic layers were washed with H2O, dried over MgSO4, filtered and concentrated to give the title compound.

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with EtOAc
  3. washthe combined organic layers were washed with H2O
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a54c7847070145a9bd61ce2c050ba540
Source dataset
uspto-grants-2013_02
Patent number
US08378107B2

Reaction notes

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