3-Aminopropionitrile → N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanine N-(2-cyanoethyl)amide

Participants

Role	Name	HCID	Charge
Reactant	3-Aminopropionitrile	HCID 1647	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	(S)-2-(2,6-Dichlorobenzamido)-3-(2',6'-dimethoxy-[1,1'-biphenyl]-4-yl)propanoic acid	HCID 9912743	—
Solvent	1,2-Dichloroethane	HCID 11	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanine N-(2-cyanoethyl)amide	HCID 54074886	—

Reaction Steps

A solution of N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanine (0.17 g), HOBT (0.0.08 g), DIEA (0.19 mL) and 2-cyanoethylamine (0.03 mL) in DMF (5 mL) was stirred at room temperature under N2. EDC (0.14 g) was added after 10 min and the mixture was stirred at room temperature under N2. The mixture was diluted with water and extracted with EtOAc. The extract was washed successively with water, 1 N HCl, satd. NaHCO3 and brine, dried and evaporated to give 0.17 g of N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanine N-(2-cyanoethyl)amide. ESMS: m/z 526 (MH+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06855843B2
Source dataset	uspto-grants-2005_02
ORD ID	ord-aff3e8797c4c4264b4026d0d5839a616
Source note	uspto-grants-2005_02