98632-99-6

Usage

Uses

Used in Pharmaceutical Industry:
N-Acetyl-5-methoxy serine is used as a potential therapeutic agent for the treatment of neurological disorders and cognitive impairments, such as Alzheimer's disease and age-related cognitive decline. Its neuroprotective and antioxidant properties make it a promising candidate for these applications.
Used in Cognitive Enhancement:
N-Acetyl-5-methoxy serine is used as a cognitive enhancer to potentially improve memory and cognitive function in healthy individuals. Further research is needed to fully understand its mechanisms of action and potential medical uses in this area.

InChI:InChI=1/C6H11NO4/c1-4(8)7-5(3-11-2)6(9)10/h5H,3H2,1-2H3,(H,7,8)(H,9,10)

Upstream product

• 19794-53-7 3-methoxy-2-aminopropionic acid 
• 108-24-7 acetic anhydride 

Downstream Products

• 4219-94-7 DL-3-methoxy-alanine 
• 196601-67-9 (R)-2-N-acetamido-3-methoxypropionic acid 
• 19794-53-7 3-methoxy-2-aminopropionic acid 
• 175481-26-2 2-acetamido-N-benzyl-3-methoxypropionamide 
• 1206635-00-8 (R)-N-4-(sulfamoyl)benzyl 2-acetamido-3-methoxypropionamide 

Relevant academic research and scientific papers

PROCESS FOR PREPARING LACOSAMIDE

The present invention provides a process for the preparation of lacosamide in substantially optically pure form, which in one aspect comprises the following steps: (i) resolution of O-methyl-D,L-serine to provide O-methyl-D-serine in substantially optically pure form; (ii) acetylation of O-methyl-D-serine thereby obtained to provide the N-acetyl 10 derivative thereof in substantially optically pure form; (iii) activating the carboxy group of the compound thereby obtained; and (iv) reacting the compound thereby obtained with benzylamine.

Process for the preparation of Lacosamide including resolution of O-methyl-DL-serine

The present invention provides a process for the preparation of lacosamide in substantially optically pure form, which in one aspect comprises the following steps: (i) resolution of O-methyl-D,L-serine to provide O-methyl-D-serine in substantially optically pure form; (ii) acetylation of O-methyl-D-serine thereby obtained to provide the N-acetyl derivative thereof in substantially optically pure form; (iii) activating the carboxy group of the compound thereby obtained; and (iv) reacting the compound thereby obtained with benzylamine.

Synthesis and anticonvulsant activities of (R)-N-(4′-substituted) benzyl 2-acetamido-3-methoxypropionamides

The structure-activity relationship (SAR) for the N-benzyl group in the clinical antiepileptic agent (R)-lacosamide [(R)-N-benzyl 2-acetamido-3- methoxypropionamide, (R)-3] has been explored. Forty-three compounds were prepared and then evaluated at the National Institute of Neurological Disorders and Stroke Anticonvulsant Screening Program for seizure protection in the maximal electroshock (MES) and subcutaneous Metrazol models. Comparing activities for two series of substituted aryl regioisomers (2′, 3′, 4′) showed that 4′-modified derivatives had the highest activity. Significantly, structural latitude existed at the 4′-site. The SAR indicated that nonbulky 4′-substituted (R)-3 derivatives exhibited superb activity, independent of their electronic properties. Activities in the MES test of several compounds were comparable with or exceeded that of (R)-3 and surpassed the activities observed for the traditional antiepileptic agents phenytoin, phenobarbital, and valproate. 2009 American Chemical Society.

NOVEL PROCESS FOR THE PREPARATION OF AMINO ACID DERIVATIVES

The present patent application relates to an alternative process for the preparation of amino derivatives. In particular, the present application relates to an improved process for the manufacture of Lacosamide (LCM), (R)-2-acetamido-N-benzyl-3-methoxypropion-amide, which is useful as an anticonvulsive drug. In a particular aspect, the present invention relates to a process of manufacture of optically enriched (R)-2-acetamido-N-benzyl-3-methoxypropion-amide (I) comprising resolution of 2-acetamido-N-benzyl-3-methoxypropion-amide (II).