Reaction #1147632

ord-5df752512db2436ba69a82de4d0ccbf0

Reaction equation

COc1cc(CCO)cc(OC)c1B(O)O
2,6-Dimethoxy-4-(2-hydroxyethyl)benzeneboronic acid
CCOC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1c(Cl)cccc1Cl
N-(2,6-dichlorobenzoyl)-4-bromo-L-phenylalanine ethyl ester
→
CCOC(=O)[C@H](Cc1ccc(-c2c(OC)cc(CCO)cc2OC)cc1)NC(=O)c1c(Cl)cccc1Cl
N-(2,6-dichlorobenzoyl)-4-[2,6-dimethoxy-4-(2-hydroxyethyl)phenyl]-L-phenylalanine ethyl ester

Reactants

COc1cc(CCO)cc(OC)c1B(O)O
2,6-Dimethoxy-4-(2-hydroxyethyl)benzeneboronic acid
CCOC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1c(Cl)cccc1Cl
N-(2,6-dichlorobenzoyl)-4-bromo-L-phenylalanine ethyl ester

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

2,6-Dimethoxy-4-(2-hydroxyethyl)benzeneboronic acid was coupled with N-(2,6-dichlorobenzoyl)-4-bromo-L-phenylalanine ethyl ester according to the procedure described in Example 8-3) to yield 1.3 g of N-(2,6-dichlorobenzoyl)-4-[2,6-dimethoxy-4-(2-hydroxyethyl)phenyl]-L-phenylalanine ethyl ester. ESMS: m/z 546 (MH+).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06521666B1uspto-grants-2003_02