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

Base Information

• Chemical Name: (2R)-2-amino-N-benzyl-3-hydroxypropanamide
• CAS No.: 175481-39-7
• Molecular Formula: C10H14N2O2
• Molecular Weight: 194.233
• UNII: YWX32A3SZ0
• DSSTox Substance ID: DTXSID801228150
• ChEMBL ID: CHEMBL2147167
• Mol file: 175481-39-7.mol

Synonyms:175481-39-7;Desacetyl Desmethyl Lacosamide;(2R)-2-amino-N-benzyl-3-hydroxypropanamide;YWX32A3SZ0;(2R)-2-amino-3-hydroxy-N-(phenylmethyl)propanamide;UNII-YWX32A3SZ0;Lacosamide impurity E [EP];(R)-2-amino-N-benzyl-3-hydroxypropanamide;Propanamide, 2-amino-3-hydroxy-N-(phenylmethyl)-, (2R)-;SCHEMBL47278;CHEMBL2147167;WYCNJBXJCACFCM-SECBINFHSA-N;DTXSID801228150;LACOSAMIDE IMPURITY E [EP IMPURITY];(R)-2-amino-N-benzyl-3-hydroxypropionamide;(2r)-2-amino-3-hydroxy-n-(phenylmethyl)-propanamide

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

Chemical Property:

• Melting Point: 97 - 99oC
• PSA: 75.35000
• LogP: 0.71360
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 194.105527694
• Heavy Atom Count: 14
• Complexity: 179

Purity/Quality:

95% ^*data from raw suppliers

DesacetylDesmethylLacosamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CNC(=O)C(CO)N
• Isomeric SMILES: C1=CC=C(C=C1)CNC(=O)[C@@H](CO)N
• Uses: Desacetyl Desmethyl Lacosamide is an impurity of Lacosamide (L098500) which is a potent anticonvulsant.

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

There total 11 articles about (2R)-2-amino-N-benzyl-3-hydroxypropanamide 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-(benzyloxycarbonyl)amino-3-hydroxypropionamide (219835-31-1) → (2R)-2-amino-3-hydroxy-N-(phenylmethyl)propanamide (175481-39-7)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃;

DOI:10.1021/jm100508m

Reference yield: 90.0%

tert-butyl 4-(benzylcarbamoyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate → (2R)-2-amino-3-hydroxy-N-(phenylmethyl)propanamide (175481-39-7)

Guidance literature:

With hydrogenchloride; In dichloromethane; water; at 25 - 30 ℃; for 1h;

Reference yield: 73.52%

tert-butyl-N-[(1R)-2-(benzylamino)-1-(hydroxymethyl)-2-oxo-ethyl]carbamate (1253790-58-7) → (2R)-2-amino-3-hydroxy-N-(phenylmethyl)propanamide (175481-39-7)

Guidance literature:

tert-butyl-N-[(1R)-2-(benzylamino)-1-(hydroxymethyl)-2-oxo-ethyl]carbamate; With hydrogenchloride; In dichloromethane; water; at 20 - 25 ℃;

With sodium hydroxide; In dichloromethane; water; pH=8 - 9;

upstream raw materials:

R-(-)-serine methyl ester hydrochloride

benzylamine

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

D-Serine

Downstream raw materials:

tert-butyl-N-[(1R)-2-(benzylamino)-1-(hydroxymethyl)-2-oxo-ethyl]carbamate

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

(R)-N-benzyl-2-(ethoxycarbonylamino)-3-methoxypropionamide

(R)-N-benzyl-2-(ethoxycarbonylamino)-3-hydroxypropionamide

Refernces

• 1、 -. "NOVEL PROCESS FOR THE PREPARATION OF (R)-N-BENZYL-2-ACETAMIDO-3-METHOXYPROPIONAMIDE". Paragraph 0045. . Retrieved 2014/11/11.
• 2、 -. "PROCESS FOR THE PREPARATION OF LACOSAMIDE". Paragraph 0128. . Retrieved 2013/05/22.