(R*,S*)-(1)-5-(1-Hydroxy-2-((1-methyl-3-phenylpropyl)amino)ethyl)salicylamide

Base Information

• Chemical Name: (R*,S*)-(1)-5-(1-Hydroxy-2-((1-methyl-3-phenylpropyl)amino)ethyl)salicylamide
• CAS No.: 83167-31-1
• Molecular Formula: C19H24N2O3
• Molecular Weight: 328.4055
• European Community (EC) Number: 276-692-5
• UNII: GA3AWI2QBK
• DSSTox Substance ID: DTXSID90222779
• Nikkaji Number: J291.363A
• Wikidata: Q83101102
• ChEMBL ID: CHEMBL28140
• Mol file: 83167-31-1.mol

Synonyms:(R,S)-labetolol;Labetolol, (R,S)-;GA3AWI2QBK;EINECS 276-692-5;72487-31-1;(R*,S*)-(1)-5-(1-Hydroxy-2-((1-methyl-3-phenylpropyl)amino)ethyl)salicylamide;83167-31-1;2-Hydroxy-5-((1R)-1-hydroxy-2-(((1S)-1-methyl-3-phenylpropyl)amino)ethyl)benzamide;Benzamide, 2-hydroxy-5-((1R)-1-hydroxy-2-(((1S)-1-methyl-3-phenylpropyl)amino)ethyl)-;UNII-GA3AWI2QBK;Lopac-L-1011;NCGC00016810-01;CAS-32780-64-6;CHEMBL28140;DTXSID90222779;CHEBI:167640;Benzamide, 2-hydroxy-5-(1-hydroxy-2-((1-methyl-3-phenylpropyl)amino)ethyl)-, (R-(R*,S*))-;NCGC00015595-01;NCGC00015595-02;NCGC00015595-05;(R*,S*)-(+-)-5-[1-hydroxy-2-[(1-methyl-3-phenylpropyl)amino]ethyl]salicylamide;2-hydroxy-5-[(1R)-1-hydroxy-2-{[(2S)-4-phenylbutan-2-yl]amino}ethyl]benzamide;2-Hydroxy-5-[(R)-1-hydroxy-2-[[(S)-1-methyl-3-phenylpropyl]amino]ethyl]benzamide

Chemical Property of (R*,S*)-(1)-5-(1-Hydroxy-2-((1-methyl-3-phenylpropyl)amino)ethyl)salicylamide

Chemical Property:

• Boiling Point: 552.7°Cat760mmHg
• PKA: 8.21±0.31(Predicted)
• Flash Point: 288.1°C
• PSA: 95.58000
• Density: 1.2g/cm³
• LogP: 3.22660
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 328.17869263
• Heavy Atom Count: 24
• Complexity: 385

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(CCC1=CC=CC=C1)NCC(C2=CC(=C(C=C2)O)C(=O)N)O
• Isomeric SMILES: C[C@@H](CCC1=CC=CC=C1)NC[C@@H](C2=CC(=C(C=C2)O)C(=O)N)O

Technology Process of (R*,S*)-(1)-5-(1-Hydroxy-2-((1-methyl-3-phenylpropyl)amino)ethyl)salicylamide

There total 16 articles about (R*,S*)-(1)-5-(1-Hydroxy-2-((1-methyl-3-phenylpropyl)amino)ethyl)salicylamide 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:

→ labetaol (36894-69-6,61466-67-9,61466-91-9,72487-31-1,72487-32-2,75659-07-3,83167-24-2,83167-31-1,83167-32-2)

Guidance literature:

Gemisch A/B, 1) p-Toluolsulfonsaeure, 2) Hydrolyse;

Reference yield:

→ 5-[1-Hydroxy-2-(1-methyl-3-phenylpropyl)aminoethyl]salicyamide + labetaol (36894-69-6,61466-67-9,61466-91-9,72487-31-1,72487-32-2,75659-07-3,83167-24-2,83167-31-1,83167-32-2)

Guidance literature:

Reference yield:

1-phenyl-3-butanol (2344-70-9) → labetaol (36894-69-6,61466-67-9,61466-91-9,72487-31-1,72487-32-2,75659-07-3,83167-24-2,83167-31-1,83167-32-2)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / dichloromethane / -10 - 20 °C

2: potassium carbonate / acetonitrile / 81 °C

3: palladium 10% on activated carbon; hydrogen / methanol / 8 h / 50 °C / 3750.38 Torr

With palladium 10% on activated carbon; hydrogen; potassium carbonate; triethylamine; In methanol; dichloromethane; acetonitrile;

upstream raw materials:

1-phenyl-3-butanol

5-(2-bromoacetyl)-2-hydroxybenzamide

2-hydroxy-5-<acetyl>benzamide

labetaol

Downstream raw materials:

(S,R)-labetalol

*)>-2-hydroxy-5-<1-hydroxy-2-<(1-methyl-3-phenylpropyl)amino>ethyl>benzamide

(R,R)-labetalol

2-Hydroxy-5-[1-hydroxy-2-((R)-1-methyl-3-phenyl-propylamino)-ethyl]-benzamide