Anisole → N-(2,6-dichlorobenzoyl)-4-(2-sulfamoylphenyl)-L-phenylalanine methyl ester

HRID 24633Notes

Reaction equation

HRID 24633 reaction equation
[CH3:1][O:2][C:3](=[O:37])[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:36])(=[O:35])[NH:30]C(C)(C)C)=[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].C1(OC)C=CC=CC=1>C(O)(C(F)(F)F)=O>[CH3:1][O:2][C:3](=[O:37])[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:36])(=[O:35])[NH2:30])=[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

4

Reactant 2

HCID 7519AnisoleHCID 53906758N-(2,6-Dichlorobenzoyl)-4-[2-[N-(tert-butyl)sulfamoyl]phenyl]-L-phenylalanine methyl ester

Product 1

HCID 54314607N-(2,6-dichlorobenzoyl)-4-(2-sulfamoylphenyl)-L-phenylalanine methyl esterYield 85.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

N-(2,6-Dichlorobenzoyl)-4-[2-[N-(tert-butyl)sulfamoyl]phenyl]-L-phenylalanine methyl ester (130 mg) was dissolved in TFA (2 mL), to this solution was added anisole (20 μM) and the mixture was stirred at room temperature for 6 h. TFA was removed under reduced pressure to give 100 mg of N-(2,6-dichlorobenzoyl)-4-(2-sulfamoylphenyl)-L-phenylalanine methyl ester. ESMS: m/z 507 (MH+).

Workup

  1. customTFA was removed under reduced pressure

Sources & evidence

ORD record
ord-7b797cfe25f04d8ca8ea0b068d47ea9b
Source dataset
uspto-grants-2005_02
Patent number
US06855843B2

Reaction notes

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