Reaction #52967

ord-7d54cf8a348c43769d85ac6070dedf22

Reaction equation

COc1ccc(CO)c(OC)c1B(O)O
2,6-Dimethoxy-3-(hydroxymethyl)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)ccc(CO)c2OC)cc1)NC(=O)c1c(Cl)cccc1Cl
N-(2,6-dichlorobenzoyl)-4-[2,6-dimethoxy-3-(hydroxymethyl)phenyl]-L-phenylalanine ethyl ester

Reactants

COc1ccc(CO)c(OC)c1B(O)O
2,6-Dimethoxy-3-(hydroxymethyl)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-3-(hydroxymethyl)benzeneboronic acid was coupled with N-(2,6-dichlorobenzoyl)-4-bromo-L-phenylalanine ethyl ester in a similar method as described in Example 7-2) to give N-(2,6-dichlorobenzoyl)-4-[2,6-dimethoxy-3-(hydroxymethyl)phenyl]-L-phenylalanine ethyl ester.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06855843B2uspto-grants-2005_02