Eugenol → Amino-acetic acid 4-allyl-2-methoxy-phenyl ester

Participants

Role	Name	HCID	Charge
Reactant	Eugenol	HCID 3314	—
Reactant	4-Methylmorpholine	HCID 7972	—
Reactant	N-(tert-butoxycarbonyl)glycine	HCID 78288	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Solvent	Dichloromethane	HCID 6344	—
Product	Amino-acetic acid 4-allyl-2-methoxy-phenyl ester	HCID 69920127	74.5%

Reaction Conditions

Temperature	25 °C

Reaction Steps

To a solution of Eugenol (0.3 g, 1.82 mmol) in DCM (20 mL), was added Boc-glycine (0.35 g, 2.01 mmol), N-methyl morpholine (0.65 mL, 6.00 mmol), EDC.HCl (0.76 g, 4.0 mmol) and DMAP at ice temperature. The mixture was allowed to stir at room temperature (25° C.) over a period of 12 h. The resulting mixture was diluted with DCM (100 mL), washed with water (2×50 mL) and dried over sodium sulphate. The crude product obtained upon evaporation of the solvent was purified by silica gel column chromatography to obtain resulting product as pale yellow oil (300 mg, 46.9%)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08846721B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-20563f5d9d02499d865f4a5bbbe742c0
Source note	uspto-grants-2014_09