Reaction #1147631

Reaction equation

2,6-dimethoxy-4-(thiomorpholinomethyl)benzeneboronic acid

N-(2,6-dichlorobenzoyl)-4bromo-L-phenylalanine ethyl ester

K2CO3

→

N-(2,6-dichlorobenzoyl)-4-[2,6-dimethoxy-4-(thiomorpholinomethyl)phenyl]-L-phenylalanine ethyl ester

Yield 15.2%

Solvents

DME H2O

Conditions

Workup

1. 1
   Otherpurified

Procedure

A mixture of 2,6-dimethoxy-4-(thiomorpholinomethyl)benzeneboronic acid (1.1 g), N-(2,6-dichlorobenzoyl)-4bromo-L-phenylalanine ethyl ester (0.71 g), Pd(PPh3)4 (1.0 g) and K2CO3 (1.00 g) in DME/H2O (10 mL/0.5 mL) was heated at 80° C. for 6 h under N2. The mixture was worked up and purified according to the procedure described in Example 8-3) to yield 0.15 g of N-(2,6-dichlorobenzoyl)-4-[2,6-dimethoxy-4-(thiomorpholinomethyl)phenyl]-L-phenylalanine ethyl ester. mp. 86-89° C. ESMS: m/z 616 (MH+). HCl salt: mp. 204-205° C.

Source