Chlorosulfonyl isocyanate → N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxy-3-carbamoylphenyl)-L-phenylalanine methyl ester
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[C:28]([O:29][CH3:30])=[CH:27][CH:26]=[CH:25][C:24]=2[O:31][CH3:32])=[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].ClS([N:38]=[C:39]=[O:40])(=O)=O>CC#N>[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[C:24]([O:31][CH3:32])=[CH:25][CH:26]=[C:27]([C:39](=[O:40])[NH2:38])[C:28]=2[O:29][CH3:30])=[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]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
N-(2,6-Dichlorobenzoyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanine methyl ester (150 mg) was dissolved in MeCN (6 mL) under N2 and chlorosulfonyl isocyanate (45 μL) was added, and the mixture was stirred at room temperature for 2.5 h. The mixture was concentrated and 1N HCl (8 mL) was added. The mixture was stirred at room temperature overnight, extracted with AcOEt, dried (MgSO4), filtered and evaporated. The crude product was purified by preparative TLC (silica gel; eluent: AcOEt) to give N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxy-3-carbamoylphenyl)-L-phenylalanine methyl ester (156 mg).