(R)-2-amino-N-benzyl-3-methoxypropanamide

Base Information

• Chemical Name: (R)-2-amino-N-benzyl-3-methoxypropanamide
• CAS No.: 196601-69-1
• Molecular Formula: C11H16N2O2
• Molecular Weight: 208.26
• Hs Code.: 2922500090
• UNII: R88M5U8KUE
• DSSTox Substance ID: DTXSID40435655
• Nikkaji Number: J1.029.116J
• Wikidata: Q72438185
• ChEMBL ID: CHEMBL1852815
• Mol file: 196601-69-1.mol

Synonyms:196601-69-1;(R)-2-amino-N-benzyl-3-methoxypropanamide;(2R)-2-amino-N-benzyl-3-methoxypropanamide;(R)-2-Amino-N-benzyl-3-methoxypropionamide;Desacetyl lacosamide;Propanamide, 2-amino-3-methoxy-N-(phenylmethyl)-, (2R)-;Descarbonyl-lacosamide;(2R)-2-amino-3-methoxy-N-(phenylmethyl)Propanamide;Lacosamide metabolite M5;R88M5U8KUE;N-benzyl-O-methyl-D-serinamide;SPM 6912;Descarbonyl Lacosamide;(2R)-2-amino-N-benzyl-3-methoxy-propanamide;UNII-R88M5U8KUE;Lacosamide impurity D [EP];SCHEMBL42109;O-Methyl-N-benzyl-D-serinamide;CHEMBL1852815;DTXSID40435655;CHEBI:169908;WPLANNRKFDHEKD-SNVBAGLBSA-N;WHA60169;MFCD14708219;AKOS015888804;AC-31111;PS-11266;LACOSAMIDE IMPURITY D [EP IMPURITY];(R)-N-benzyl-2-amino-3-methoxypropionamide;A4304;BB 0262009;J-012713

Chemical Property of (R)-2-amino-N-benzyl-3-methoxypropanamide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.535
• Boiling Point: 421.947 °C at 760 mmHg
• PKA: 15.04±0.46(Predicted)
• Flash Point: 208.986 °C
• PSA: 64.35000
• Density: 1.107 g/cm³
• LogP: 1.36770
• Storage Temp.: 2-8°C(protect from light)
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Sonicated)
• XLogP3: 0
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 208.121177757
• Heavy Atom Count: 15
• Complexity: 191

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COCC(C(=O)NCC1=CC=CC=C1)N
• Isomeric SMILES: COC[C@H](C(=O)NCC1=CC=CC=C1)N
• Uses: (R)-2-Amino-N-benzyl-3-methoxypropionamide is an impurity of Lacosamide which is a potent anticonvulsant.

Technology Process of (R)-2-amino-N-benzyl-3-methoxypropanamide

There total 36 articles about (R)-2-amino-N-benzyl-3-methoxypropanamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(R)-N-benzyl 2-N-(benzylcarboxycarbonyl)amino-3-methoxypropionamide (196601-68-0) → (R)-2-amino-N-benzyl-3-methoxypropanamide (196601-69-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 3h; Ambient temperature;

DOI:10.1016/S0957-4166(98)00403-0

Reference yield: 100.0%

tert-butyl [(2R)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl]carbamate (880468-89-3) → (R)-2-amino-N-benzyl-3-methoxypropanamide (196601-69-1)

Guidance literature:

With hydrogenchloride; water; In dichloromethane; at 0 - 30 ℃; for 2h;

Reference yield: 95.0%

C17H19N3O4 → (R)-2-amino-N-benzyl-3-methoxypropanamide (196601-69-1)

Guidance literature:

C₁₇H₁₉N₃O₄; With 5%-palladium/activated carbon; hydrogen; In ethyl acetate; at 20 ℃; for 4h; under 760.051 Torr;

With [bis(acetoxy)iodo]benzene; In acetonitrile; at 0 ℃; for 0.5h;

With sulfuric acid; at 20 ℃; for 1h; enantioselective reaction;

DOI:10.1007/s11426-019-9606-2

upstream raw materials:

(R)-N-benzyl 2-N-(benzylcarboxycarbonyl)amino-3-methoxypropionamide

benzylamine

(R)-N-benzyl 2-N-(benzyloxycarbonyl)amino-3-hydroxypropionamide

tert-butyl [(2R)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl]carbamate

Downstream raw materials:

lacosamide

(2S)-2-(acetylamino)-N-benzyl-3-methoxypropanamide