Reacción #52951

Ecuación de reacción

NH4Cl

N-(2,6-dichlorobenzoyl)-O-(trifluoromethane sulfonyl)-L-tyrosine methyl ester

trimethyl(2-cyano-3-thienyl)tin

LiCl

→

N-(2,6-dichlorobenzoyl)-4-(2-cyano-3-thienyl)-L-phenylalanine methyl ester

Rendimiento 38.0%

Disolventes

AcOEt

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGAfter stirring at room temperature for 1 h
2. 2
   Filtraciónthe mixture was filtered through Celite
3. 3
   Lavadowashed with AcOEt
4. 4
   LavadoThe combined organic layers were washed successively with water and brine
5. 5
   Secadodried (MgSO4)
6. 6
   Otroevaporated under reduced pressure
7. 7
   OtroThe residue was purified by silica gel chromatography

Procedimiento

A mixture of N-(2,6-dichlorobenzoyl)-O-(trifluoromethane sulfonyl)-L-tyrosine methyl ester (361 mg), trimethyl(2-cyano-3-thienyl)tin (393 mg), Pd(PPh3)4 (42 mg) and LiCl (93 mg) in dioxane (8 mL) was stirred at 100° C. under N2 for 38 h. The mixture was diluted with AcOEt and treated with 10% NH4Cl aqueous solution (6 mL). After stirring at room temperature for 1 h, the mixture was filtered through Celite and washed with AcOEt. The combined organic layers were washed successively with water and brine, dried (MgSO4) and evaporated under reduced pressure. The residue was purified by silica gel chromatography to afford N-(2,6-dichlorobenzoyl)-4-(2-cyano-3-thienyl)-L-phenylalanine methyl ester (126 mg). ESMS m/z 481 (M++Na), 459 (MH+), 457 (M−H)−.

Fuente