Potassium Carbonate → N-(2,6-dichlorobenzoyl)-4-[2,6-dimethoxy-4-(thiomorpholinomethyl)phenyl]-L-phenylalanine ethyl ester

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	2,6-Dimethoxy-4-(thiomorpholinomethyl)benzeneboronic acid	HCID 22571709	—
Reactant	(S)-Ethyl 3-(4-bromophenyl)-2-(2,6-dichlorobenzamido)propanoate	HCID 54106344	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	Water 1,2-dimethoxyethane	HCID 18180031	—
Product	N-(2,6-dichlorobenzoyl)-4-[2,6-dimethoxy-4-(thiomorpholinomethyl)phenyl]-L-phenylalanine ethyl ester	HCID 54065008	15.2%

Reaction Conditions

Temperature	80 °C

Reaction Steps

A mixture of 2,6-dimethoxy-4-(thiomorpholinomethyl)-benzeneboronic acid (1.1 g), N-(2,6-dichlorobenzoyl)-4-bromo-L-phenylalanine ethyl ester (0.71 g), Pd(PPh3)4 (1.0 g) and K2CO3 (1.00 g) in DME/H2O (10 mL/0.5 mL) was heated at 80° C. for 6 h under N2. The mixture was worked up and purified according to the procedure described in Example 8-3) to yield 0.15 g of N-(2,6-dichlorobenzoyl)-4-[2,6-dimethoxy-4-(thiomorpholinomethyl)phenyl]-L-phenylalanine ethyl ester. mp. 86-89° C. ESMS: m/z 616 (MH+). HCl salt: mp. 204-205° C.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06855843B2
Source dataset	uspto-grants-2005_02
ORD ID	ord-f99ab618a70f43b898de3389cea6b161
Source note	uspto-grants-2005_02