Sodium Hydroxide → 3-[1-Benzyl-3-(4-cyano-phenyl)-ureidomethyl]-benzoic acid

HRID 418359

Reaction equation

HRID 418359 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=2)=[O:13])[CH:5]=1.[OH-].[Na+]>C1COCC1.CO>[CH2:23]([N:11]([CH2:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[C:3]([OH:30])=[O:2])[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=1)=[O:13])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 591908863-[1-Benzyl-3-(4-cyano-phenyl)-ureidomethyl]-benzoic acid methyl ester

Product 1

HCID 591908653-[1-Benzyl-3-(4-cyano-phenyl)-ureidomethyl]-benzoic acidYield 97.6%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Dissolved to 3-[1-benzyl-3-(4-cyano-phenyl)-ureidomethyl]-benzoic acid methyl ester (106 mg, 0.27 mmol) in 1:1 mixture of THF/MeOH (4 mL). To this was added a 15% NaOH solution and the mixture stirred overnight at room temperature. LC-MS analysis indicated the desired carboxylic acid. Concentrated the mixture and the residue was suspended in 5 mL of H2O and made acidic by the addition of 5% HCl, resulting in a white ppt., which was filtered and dried to give 101.6 mg of 3-[1-benzyl-3-(4-cyano-phenyl)-ureidomethyl]-benzoic acid.

Workup

  1. concentrationConcentrated the mixture
  2. additionmade acidic by the addition of 5% HCl
  3. customresulting in a white ppt
  4. filtration, which was filtered
  5. customdried

Sources & evidence

ORD record
ord-79fdfb1824034d099da59c90f4e00ae3
Source dataset
uspto-grants-2012_01
Patent number
US08093266B2

Linked notes

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