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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1844772Generated: October 31, 2026

Acetic Anhydride → Lacosamide

https://huagongshe.com/reaction/1844772

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AnhydrideHCID 7918—
Reactant(R)-2-Amino-N-benzyl-3-methoxypropionamideHCID 10104501—
SolventDichloromethaneHCID 6344—
SolventEthyl AcetateHCID 8857—
ProductLacosamideHCID 21907868.6%

Reaction Steps

To a cold solution (−2° C.) of 1.94 g of Intermediate 6, in 40 mL of dichloromethane was added dropwise 2.12 g of acetic anhydride maintaining the temperature below 5° C. The reaction mixture was stirred at room temperature for 3 hours and the organic phase was washed with water (2×20 mL), sodium bicarbonate solution (2×20 mL), brine and dried over sodium sulfate. The solvent was removed under vacuum and a white solid was obtained. The product was dissolved in 20 mL of ethyl acetate at reflux temperature and cooled slowly to 0° C. The solid was collected by filtration and dried yielding 1.6 g of lacosamide as a white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08946477B2
Source datasetuspto-grants-2015_02
ORD IDord-c67051dab2e04d41a3085fbaa32899af
Source noteuspto-grants-2015_02