Sodium Hydroxide → HCID 67138197, compound

HRID 1592036Notes

Reaction equation

HRID 1592036 reaction equation
C[O:2][C:3](=[O:33])[CH:4]([NH:23][C:24](=[O:32])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[NH2:31])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:7]=1.[OH-].[Na+]>CO>[NH2:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C:24]([NH:23][CH:4]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:7]=1)[C:3]([OH:33])=[O:2])=[O:32]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67138465HCID 67138465, compound

Product 1

HCID 67138197HCID 67138197, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the title H compound, 2-(2-amino-benzoylamino)-3-(3-benzyloxy-4-nitro-phenyl)-propionic acid methyl ester (388 mg, 0.863 mmol) in methanol (8 mL) is added 1N aqueous NaOH (1.73 mL, 1.73 mmol) and the mixture is stirred at RT for 2 h and evaporated. The residue is dissolved in water (20 mL) and the solution is washed twice with EtOAc. The aqueous layer is neutralized with 1N aqueous HCl (1.73 mL) and extracted three times with EtOAc. The organic extracts are washed with brine, dried over anhydrous MgSO4, decolorized with charcoal, filtered and evaporated to give 2-(2-amino-benzoylamino)-3-(3-benzyloxy-4-nitro-phenyl)-propionic acid as a viscous yellow oil: [M+1]+=436, [M−1]−=434.

Workup

  1. customevaporated
  2. dissolutionThe residue is dissolved in water (20 mL)
  3. washthe solution is washed twice with EtOAc
  4. extractionextracted three times with EtOAc
  5. washThe organic extracts are washed with brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-6fc2fa652a6243f5a39f8c4c2d76266c
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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