(1S,2S)-(+)-Pseudoephedrinepropionamide

Base Information

• Chemical Name: (1S,2S)-(+)-Pseudoephedrinepropionamide
• CAS No.: 159213-03-3
• Molecular Formula: C13H19 N O2
• Molecular Weight: 221.299
• DSSTox Substance ID: DTXSID10456635
• Nikkaji Number: J609.872J
• Wikidata: Q82279192
• Mol file: 159213-03-3.mol

Synonyms:(1S,2S)-(+)-Pseudoephedrinepropionamide;159213-03-3;N-[(1S,2S)-1-hydroxy-1-phenylpropan-2-yl]-N-methylpropanamide;(1S 2S)-(+)-PSEUDOEPHEDRINEPROPIONAMIDE;SCHEMBL6908215;DTXSID10456635;(s,s)-pseudoephedrine propionamide;AKOS015913051;(1S,2S)-(+)-Pseudoephedrinepropionamide, 98%;J-009579;N-Methyl-N-[(alphaS,betaS)-alpha-methyl-beta-hydroxyphenethyl]propanamide

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Chemical Property of (1S,2S)-(+)-Pseudoephedrinepropionamide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 114-118 °C(lit.)
• Refractive Index: 1.53
• Boiling Point: 374.1°Cat760mmHg
• PKA: 13.70±0.20(Predicted)
• Flash Point: 180.1°C
• PSA: 40.54000
• Density: 1.065g/cm³
• LogP: 1.97690
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 221.141578849
• Heavy Atom Count: 16
• Complexity: 224

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(=O)N(C)C(C)C(C1=CC=CC=C1)O
• Isomeric SMILES: CCC(=O)N(C)[C@@H](C)[C@H](C1=CC=CC=C1)O

Technology Process of (1S,2S)-(+)-Pseudoephedrinepropionamide

There total 4 articles about (1S,2S)-(+)-Pseudoephedrinepropionamide 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: 97.0%

pseudoephedrine (90-82-4,7009-81-6,90-83-5,6912-63-6) + propionic acid anhydride (123-62-6) → N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide (159213-03-3)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1021/jo102038q

Reference yield: 95.0%

→ N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide (159213-03-3) + Propionamid (79-05-0)

Guidance literature:

Reference yield: 92.0%

pseudoephedrine (90-82-4,7009-81-6,90-83-5,6912-63-6) + propionyl chloride (79-03-8) → N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide (159213-03-3)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1021/ol902221y

upstream raw materials:

pseudoephedrine

propionic acid anhydride

propanoic acid methyl ester

propionyl chloride

Downstream raw materials:

(2R,4R,6S)-7-Benzyloxy-2,4,6-trimethyl-heptanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

(R)-N-[(1S,2S)-1-hydroxy-1-phenylpropan-2-yl]-N,2'-dimethylpent-4-enamide

(2R,4S)-5-(tert-butyldiphenylsilyloxy)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4-trimethylpentanamide

(1'S,2'S,2R)-4-benzyloxy-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-2,N-dimethylbutyramide