Dimethylformamide → N(2,6-dichlorobenzoyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanyl chloride

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Oxalyl chloride	HCID 65578	—
Reactant	(S)-2-(2,6-Dichlorobenzamido)-3-(2',6'-dimethoxy-[1,1'-biphenyl]-4-yl)propanoic acid	HCID 9912743	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	N(2,6-dichlorobenzoyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanyl chloride	HCID 54238962	—

Reaction Conditions

Temperature	0 °C

Reaction Steps

To a solution of N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanine (0.1 g) in THF (5 mL) at 0° C. under N2 was added oxalyl chloride (0.055 mL) followed by a drop of DMF. The solution was stirred at 0° C. for 2 h followed by stirring at room temperature for 2 h. THF was evaporated and fresh THF (5 mL) was added and the solution was evaporated again. This process was repeated one more time and the residue was dried under vacuum to yield N(2,6-dichlorobenzoyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanyl chloride.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06521666B1
Source dataset	uspto-grants-2003_02
ORD ID	ord-3ab7fab670a14558889389c7e1d213e3
Source note	uspto-grants-2003_02