Potassium bisulfate → N-(2,6-dichlorobenzoyl)-3-[2-(2,6-dichlorophenyl)-6-quinolyl]alanine

HRID 1869783Notes

Reaction equation

HRID 1869783 reaction equation
[Cl:1][C:2]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[C:3]=1[C:4]([NH:6][CH:7]([CH2:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[C:18]([C:23]1[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:24]=1[Cl:30])[CH:17]=[CH:16]2)[C:8]([O:10]C)=[O:9])=[O:5].OS([O-])(=O)=O.[K+]>CC#N.O.[OH-].[Na+]>[Cl:1][C:2]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[C:3]=1[C:4]([NH:6][CH:7]([CH2:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[C:18]([C:23]1[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:24]=1[Cl:30])[CH:17]=[CH:16]2)[C:8]([OH:10])=[O:9])=[O:5]

Participants

4

Reactant 2

HCID 516920Potassium bisulfateHCID 10482608methyl N-(2,6-dichlorobenzoyl)-3-[2-(2,6-dichlorophenyl)-6-quinolyl]alaninate

Product 1

HCID 10052832N-(2,6-dichlorobenzoyl)-3-[2-(2,6-dichlorophenyl)-6-quinolyl]alanine

Reagents, catalysts & solvents 1

HCID 86619053CH3CN H2O NaOHSolvent

Procedure

Methyl 2-[(2,6-dichlorobenzoyl)amino]-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoate 35 (0.2 g) is solubilized in CH3CN/H2O/NaOH 0.1N (4 ml/0.22 ml/3.65 ml). After 1 night at room temperature, 10% KHSO4 (9 ml) is added and CH3CN is evaporated. The resulting aqueous phase is extracted two times with AcOEt (2×12 ml). The organic phase is washed with brine, dried over MgSO4 and evaporated under vacuum. The residue is purified by silica gel chromatography using CH2Cl2/CH3OH/NH4OH cc (90/10/1) as eluent.

Workup

  1. waitAfter 1 night at room temperature
  2. customCH3CN is evaporated
  3. extractionThe resulting aqueous phase is extracted two times with AcOEt (2×12 ml)
  4. washThe organic phase is washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated under vacuum
  7. customThe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-a7b5270c05ae4f46bb823d186fbe8612
Source dataset
uspto-grants-2009_12
Patent number
US07638630B2

Reaction notes

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