Benzoyl chloride → N-(2,6-dichlorobenzoyl)-4-[2-(N-benzoylsulfamoyl)phenyl]-L-phenylalanine methyl ester

HRID 24634Notes

Reaction equation

HRID 24634 reaction equation
[CH3:1][O:2][C:3](=[O:33])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[S:29](=[O:32])(=[O:31])[NH2:30])=[CH:19][CH:18]=1)[NH:5][C:6](=[O:15])[C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:14].[C:34](Cl)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.CCOC(C)=O.C([O-])(O)=O.[Na+]>N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:33])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[S:29](=[O:32])(=[O:31])[NH:30][C:34](=[O:41])[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:19][CH:18]=1)[NH:5][C:6](=[O:15])[C:7]1[C:8]([Cl:14])=[CH:9][CH:10]=[CH:11][C:12]=1[Cl:13]

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 54314607N-(2,6-dichlorobenzoyl)-4-(2-sulfamoylphenyl)-L-phenylalanine methyl ester

Product 1

HCID 54236278N-(2,6-dichlorobenzoyl)-4-[2-(N-benzoylsulfamoyl)phenyl]-L-phenylalanine methyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

N-(2,6-Dichlorobenzoyl)-4-(2-sulfamoylphenyl)-L-phenylalanine methyl ester (100 mg) was dissolved in anhydrous pyridine (5 mL). To this solution was added benzoyl chloride (50 μL) and the mixture was stirred for 12 h at room temperature under N2. EtOAc and satd. NaHCO3 were added to the mixture and the EtOAc phase was washed with 1 N HCl, dried (MgSO4) and evaporated. The residue was purified by flash column chromatography (silica gel; eluent: EtOAc/hexanes 1:2) to give N-(2,6-dichlorobenzoyl)-4-[2-(N-benzoylsulfamoyl)phenyl]-L-phenylalanine methyl ester.

Workup

  1. washthe EtOAc phase was washed with 1 N HCl
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by flash column chromatography (silica gel; eluent: EtOAc/hexanes 1:2)

Sources & evidence

ORD record
ord-ae8f278449894fc1a6c001c76fbac893
Source dataset
uspto-grants-2005_02
Patent number
US06855843B2

Reaction notes

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