Potassium Carbonate → N-(2,6-Dichlorobenzoyl)-4-[2-[N-(tert-butyl)sulfamoyl]phenyl]-L-phenylalanine methyl ester

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	Boronic acid, B-(2-(((1,1-dimethylethyl)amino)sulfonyl)phenyl)-	HCID 4997616	—
Reactant	N-(2,6-dichlorobenzoyl)-4-bromo-L-phenylalanine methyl ester	HCID 54284267	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	Water	HCID 962	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	N-(2,6-Dichlorobenzoyl)-4-[2-[N-(tert-butyl)sulfamoyl]phenyl]-L-phenylalanine methyl ester	HCID 53906758	76.5%

Reaction Conditions

Temperature	80 °C

Reaction Steps

2-[N-(tert-Butyl)sulfamoyl]benzeneboronic acid (0.4 g) was dissolved in DME (10 mL). To this solution was added K2CO3 (0.1 g), N-(2,6-dichlorobenzoyl)-4-bromo-L-phenylalanine methyl ester (0.1 g), Pd(Ph3P)4 (0.1 g) and water (0.2 mL). The mixture was heated at 80° C. overnight. After cooling, EtOAc and water were added to the mixture. The EtOAc phase was dried (MgSO4), filtered and evaporated. The residue was purified by flash column chromatography (silica gel; eluent: EtOAc/hexanes 1:2) to give 100 mg of the title compound. ESMS: m/z 585 ([M+Na]+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06521666B1
Source dataset	uspto-grants-2003_02
ORD ID	ord-309d75aaf36a4294a0719041d691f7e4
Source note	uspto-grants-2003_02