Reaction #52936

Reaction equation

2,6-dicyanobenzene boronic acid

K2CO3

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

→

N-(2,6-dichlorobenzoyl)-4-(2-cyano-6-carbamoyl-phenyl)-L-phenylalanine methyl ester

Yield 65.5%

Solvents

DME H2O

EtOAc

Conditions

Workup

1. 1
   TemperatureThe mixture was cooled
2. 2
   Washwashed successively with water and brine
3. 3
   DryingThe organic layer was dried (MgSO4)
4. 4
   Otherevaporated
5. 5
   Otherthe residue was purified by column chromatography (silica gel; eluent: EtOAc/hexane 3/1))

Procedure

To a mixture of 2,6-dicyanobenzene boronic acid (0.516 g) and anhydrous K2CO3 (0.52 g) in DME/H2O (10 mL/0.5 mL) under N2 was added N-(2,6-dichlorobenzoyl)-O-(trifluoromethanesulfonyl)-L-tyrosine methyl ester (0.5 g), The catalyst Pd(PPh3)4 (0.1 g) was added and the mixture was heated at 80° C. for 5 h. The mixture was cooled, diluted with EtOAc and washed successively with water and brine. The organic layer was dried (MgSO4), evaporated, and the residue was purified by column chromatography (silica gel; eluent: EtOAc/hexane 3/1)) to yield 325 mg of N-(2,6-dichlorobenzoyl)-4-(2-cyano-6-carbamoyl-phenyl)-L-phenylalanine methyl ester. ESMS: m/z 496 (MH+), 494 (M−H)−.

Source