Acetic Anhydride → Lacosamide

반응식

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]

참가 물질

반응물 3

HCID 7918Acetic Anhydride

HCID 31263Propionic anhydride

HCID 67362298(R)-N-Benzyl-3-methoxy-2-propionamidopropanamide

생성물 1

HCID 219078Lacosamide

실험 절차

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.

출처 및 근거

ORD 기록: ord-547efe3e769043cf99775ee30feb0730
출처 데이터셋: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08853453B2

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