Potassium Carbonate → N-tert-butoxycarbonyl-4-(2,6-dimethoxyphenyl)-L-phenylalanine methyl ester

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	(2,6-Dimethoxyphenyl)boronic acid	HCID 2734343	—
Reactant	(S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(4-(((trifluoromethyl)sulfonyl)oxy)phenyl)propanoate	HCID 10455198	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	Water	HCID 962	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	N-tert-butoxycarbonyl-4-(2,6-dimethoxyphenyl)-L-phenylalanine methyl ester	HCID 10309931	97.7%

Reaction Conditions

Temperature	80 °C

Reaction Steps

2,6-Dimethoxybenzeneboronic acid (0.5 g) was dissolved in DME (10 mL). To the solution was added K2CO3 (0.7 g), N-(tert-butoxycarbonyl)-O-(trifluoromethane-sulfonyl)-L-tyrosine methyl ester (0.4 g), Pd(Ph3P)4 (0.6 g) and water (0.2 mL). The resulting mixture was heated to 80° C. overnight. Subsequently EtOAc and water were added to the mixture. The EtOAc layer was dried (MgSO4) and evaporated. The residue was purified by flash column chromatography (silica gel; eluent: EtOAc/hexane 1:2) to give N-(tert-butoxycarbonyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanine methyl ester (380 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06855843B2
Source dataset	uspto-grants-2005_02
ORD ID	ord-ed9c09b43732410cac601d6ce68c8ca5
Source note	uspto-grants-2005_02