1,2-Dichloroethane → N-[2(S)-([1-(4-Cyanobenzyl)-1H-imidazol-5-yl]acetylamino)-3(S)-methylpentyl]-N-(1-naphthylmethyl) glycine methyl ester

Participants

Role	Name	HCID	Charge
Reactant	1,2-Dichloroethane	HCID 11	—
Reactant	4-Methylmorpholine	HCID 7972	—
Reactant	3-hydroxy-1,2,3-benzotriazin-4(3H)-one	HCID 73026	—
Reactant	1-(4-Cyanobenzyl)imidazole-5-acetic acid	HCID 18433630	—
Reactant	N-[2(S)-(amino)-3(S)-methylpentyl]-N-(1-naphthylmethyl)glycine methyl ester hydrochloride	HCID 70338221	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	N-[2(S)-([1-(4-Cyanobenzyl)-1H-imidazol-5-yl]acetylamino)-3(S)-methylpentyl]-N-(1-naphthylmethyl) glycine methyl ester	HCID 67572382	—

Reaction Steps

To a solution of [1-(4-cyanobenzyl)-1H-imidazol-5-yl]acetic acid. (4.09 g, 10.24 mmol), the amine hydrochloride salt from step E (5.07 g, 10.24 mmol), HOOBT (1.67 g, 10.24 mmol), and N-methylmorpholine (2.36 ml, 21.5 mmol) in DMF (50 ml) at 0° C., was added EDC (2.16 g, 11.26 mmol). The reaction was stirred at room temperature for 18 hrs, diluted with EtOAc and the organic layer washed with sat. aq NaHCO3, brine, dried (Na2SO4), and the solvent evaporated in vacuo. The residue was chromatographed (SiO2, 3-4% MeOH in CH2Cl2) to afford the title compound as a white solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05652257
Source dataset	uspto-grants-1997_07
ORD ID	ord-caa95c38e07e4591af8d22dfde1951c7
Source note	uspto-grants-1997_07