Reaction #1147630

Reaction equation

2,6-dimethoxy-4-[(t-butyldiphenylsilyloxy)methyl]benzeneboronic acid

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

K2CO3

→

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

Yield 97.9%

Solvents

DME H2O

Conditions

Workup

1. 1
   Otherpurified in a similar procedure

Procedure

A mixture of 2,6-dimethoxy-4-[(t-butyldiphenylsilyloxy)methyl]benzeneboronic acid (5.2 g), N-(2,6-dichlorobenzoyl)-4-bromo-L-phenylalanine ethyl ester (1.71 g), Pd(PPh3)4 (0.44 g) and K2CO3 (1.59 g) in DME/H2O (20 mL/0.5 mL) was heated at 80° C. for 24 h under N2. The mixture was worked up and purified in a similar procedure as described in Example 8-3) to yield 2.9 g of N-(2,6-dichlorobenzoyl)-4-[2,6-dimethoxy-4-[(t-butyldiphenylsilyloxy)methyl]phenyl]-L-phenylalanine ethyl ester. ESMS: m/z 770 (MH+).

Source