Reacción #52970

Ecuación de reacción

N-(2,6-Dichlorobenzoyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanine methyl ester

chlorosulfonyl isocyanate

→

N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxy-3-carbamoylphenyl)-L-phenylalanine methyl ester

Disolventes

MeCN

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe mixture was concentrated
2. 2
   workup.ADDITION1N HCl (8 mL) was added
3. 3
   workup.STIRRINGThe mixture was stirred at room temperature overnight
4. 4
   Extracciónextracted with AcOEt
5. 5
   Secadodried (MgSO4)
6. 6
   Filtraciónfiltered
7. 7
   Otroevaporated
8. 8
   OtroThe crude product was purified by preparative TLC (silica gel; eluent: AcOEt)

Procedimiento

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).

Fuente