Reaction #52954
ord-824d2a35964a4bd89f4153a27616c53e
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%
Reactants
Reagents
None
Solvents
Conditions
Temperature
80°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.
Workup
- 1Otherpurified 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(Ph3)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+).