Acetic Anhydride → Lacosamide

HRID 534694Notes

Reaction equation

HRID 534694 reaction equation
C(OC(=O)C)(=O)C.C(OC(=O)CC)(=O)CC.[C:17]([NH:21][C@H:22]([CH2:33][O:34][CH3:35])[C:23]([NH:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])(=[O:20])[CH2:18]C>>[CH3:18][C:17]([NH:21][C@@H:22]([C:23]([NH:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:24])[CH2:33][O:34][CH3:35])=[O:20]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 31263Propionic anhydrideHCID 67362298N-DescarboxyMethyl-N-carboxyethyl LacosaMide (IMpurity)

Product 1

HCID 219078Lacosamide

Procedure

The present inventors also observed that commercially available acetic anhydride contained some percentage of propanoic anhydride. As a result, during the last acetylation step (figure I), (2R)-2-propanoylamino-N-benzyl-3-methoxypropionamide of Formula III (hereinafter referred as “Impurity-B”) is obtained as an impurity along with lacosamide.

Sources & evidence

ORD record
ord-547efe3e769043cf99775ee30feb0730
Source dataset
uspto-grants-2014_10
Patent number
US08853453B2

Reaction notes

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