Lithium Hydroxide → (5-{2-[(N-Benzyl-N-cyclopropanecarbonyl-amino)-methyl]-4-cyano-phenyl}-pyridin-3-yl)-acetic acid

HRID 554593Notes

Reaction equation

HRID 554593 reaction equation
C([O:3][C:4](=[O:34])[CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][C:13]=2[CH2:20][N:21]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]([CH:24]2[CH2:26][CH2:25]2)=[O:23])[CH:11]=1)C.[Li+].[OH-]>CO>[CH2:27]([N:21]([CH2:20][C:13]1[CH:14]=[C:15]([C:18]#[N:19])[CH:16]=[CH:17][C:12]=1[C:10]1[CH:11]=[C:6]([CH2:5][C:4]([OH:34])=[O:3])[CH:7]=[N:8][CH:9]=1)[C:22]([CH:24]1[CH2:26][CH2:25]1)=[O:23])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67212964(5-{2-[(Benzyl-cyclopropanecarbonyl-amino)-methyl]-4-cyano-phenyl}-pyridin-3-yl)-acetic acid ethyl ester

Product 1

HCID 45138331(5-{2-[(N-Benzyl-N-cyclopropanecarbonyl-amino)-methyl]-4-cyano-phenyl}-pyridin-3-yl)-acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(5-{2-[(N-Benzyl-N-cyclopropanecarbonyl-amino)-methyl]-4-cyano-phenyl}-pyridin-3-yl)-acetic acid ethyl ester (0.1 g, 0.22 mmol) was dissolved in MeOH (10 mL) and treated with 1N aqueous LiOH (1 mL) dropwise. The reaction was stirred at room temperature for 1 hour, and then quenched with 1N aqueous HCl (1 ml) and extracted with EtOAc. The combined organic layers were dried and concentrated to give Compound 3.

Workup

  1. customquenched with 1N aqueous HCl (1 ml)
  2. extractionextracted with EtOAc
  3. customThe combined organic layers were dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a707b20cdedd4a61b8b14903d25fa45a
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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