Esatenolol

Base Information

• Chemical Name: Esatenolol
• CAS No.: 93379-54-5
• Molecular Formula: C14H22N2O3
• Molecular Weight: 266.34
• Hs Code.: 2924299090
• UNII: DPF757BOSR
• DSSTox Substance ID: DTXSID10239405
• Nikkaji Number: J264.929B
• Wikidata: Q24255323
• NCI Thesaurus Code: C81661
• Pharos Ligand ID: MSS8M6T72LJT
• Metabolomics Workbench ID: 54419
• ChEMBL ID: CHEMBL343633
• Mol file: 93379-54-5.mol

Synonyms:Esatenolol;(S)-Atenolol;93379-54-5;(S)-(-)-Atenolol;(-)-Atenolol;S-Atenolol;S(-)-Atenolol;Esatenolol [INN];S-(-)-Atenolol;2-(p-((2S)-2-Hydroxy-3-(isopropylamino)propoxy)phenyl)acetamide;Atenolol, (s)-;S-(-)-4-(2-Hydroxy-3-isopropylaminopropoxy)phenylacetamide;Atenolol, (-)-;(S)-4-(2-Hydroxy-3-((1-methylethyl)amino)propoxy)benzeneacetamide;UNII-DPF757BOSR;DPF757BOSR;CHEBI:31556;2-[4-[(2S)-2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]acetamide;2-{4-[(2S)-2-hydroxy-3-[(propan-2-yl)amino]propoxy]phenyl}acetamide;Benzeneacetamide, 4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)-, (S)-;(S)-(-)-4-[2-Hydroxy-3-[(1-methylethyl)amino]propoxy]benzeneacetamide;2-[4-({(2S)2-hydroxy-3-[(propan-2-yl)amino]propyl}oxy)phenyl]acetamide;SR-01000597666;S Atenolol;Benzeneacetamide, 4-[(2S)-2-hydroxy-3-[(1-methylethyl)amino]propoxy]-;BENZENEACETAMIDE, 4-((2S)-2-HYDROXY-3-((1-METHYLETHYL)AMINO)PROPOXY)-;NCGC00093636-03;atenolol-(-);CAS-56715-13-0;MFCD00074918;(S)(-)-atenolol;(S)-()-Atenolol;Tocris-0387;Tocris-0393;Esatenolol (JAN/INN);Lopac-A-142;Lopac-A-143;ESATENOLOL [JAN];(-)-4-[2-Hydroxy-3-[(1-methylethyl)amino]propoxy]benzeneacetamide;Prestwick0_000536;Prestwick1_000536;Prestwick2_000536;Prestwick3_000953;Lopac-A-7655;ESATENOLOL [MART.];SCHEMBL4363;ESATENOLOL [WHO-DD];Lopac0_000156;BSPBio_000946;MLS002153864;(S)-(-)-Atenolol, powder;SPBio_002472;(S)-(-)-Atenolol 99%;BPBio1_001042;CHEMBL343633;(S)-(-)-Atenolol, 99%;DTXSID10239405;HMS2097P08;HMS2235B16;HMS3260O14;HMS3266K19;HMS3411I05;HMS3675I05;HMS3714P08;Tox21_500156;GEO-02804;AKOS015894675;CCG-204251;CS-O-07264;DB13443;GS-0672;LP00156;SDCCGSBI-0050144.P002;NCGC00015007-01;NCGC00015007-02;NCGC00015007-03;NCGC00015007-04;NCGC00015007-05;NCGC00015007-12;NCGC00016880-01;NCGC00016880-02;NCGC00016880-03;NCGC00016880-04;NCGC00016880-05;NCGC00016880-06;NCGC00016880-07;NCGC00016880-13;NCGC00024566-01;NCGC00024570-01;NCGC00024570-02;NCGC00024570-03;NCGC00024570-04;NCGC00093636-01;NCGC00093636-02;NCGC00260841-01;LS-28558;SMR000326748;CAS-93379-54-5;A-143;AB00513856;EU-0100156;A13427;D01471;EN300-18539569;SR-01000597666-1;SR-01000597666-3;W-200527;BRD-K44993696-001-03-2;BRD-K44993696-001-05-7;Q24255323;4-((2S)-2-HYDROXY-3-((1-METHYLETHYL)AMINO)PROPOXY)BENZENEACETAMIDE

Chemical Property of Esatenolol

Chemical Property:

• Appearance/Colour: pale pink solid
• Melting Point: 148-152 °C(lit.)
• Boiling Point: 508 °Cat760mmHg
• Flash Point: 261.1 °C
• PSA: 84.58000
• Density: 1.125 g/cm³
• LogP: 1.54330
• Storage Temp.: Store at RT
• Solubility.: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: >6 mg/
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 266.16304257
• Heavy Atom Count: 19
• Complexity: 263

Purity/Quality:

99% ^*data from raw suppliers

(S)-(?)-Atenolol powder ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)NCC(COC1=CC=C(C=C1)CC(=O)N)O
• Isomeric SMILES: CC(C)NC[C@@H](COC1=CC=C(C=C1)CC(=O)N)O
• Uses: active enantiomer

Technology Process of Esatenolol

There total 32 articles about Esatenolol 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: 94.0%

isopropylamine (75-31-0) + (S)-2-(4-(3-chloro-2-hydroxypropoxy)phenyl)acetamide → (S)-Atenolol (93379-54-5)

Guidance literature:

In water; at 10 ℃; for 12h;

DOI:10.1039/c4ra16365f

Reference yield: 90.0%

isopropylamine (75-31-0) + (S)-2-(4-(3-chloro-2-hydroxypropoxy)phenyl)acetamide (56715-12-9) → (S)-Atenolol (93379-54-5)

Guidance literature:

With methanol; for 12h; Ambient temperature;

DOI:10.1248/cpb.45.412

Reference yield: 90.0%

2-(4-hydroxyphenyl)acetamide (17194-82-0) + (2s)-(+)-glycidyl 3-nitrobenzenesulfonate (115314-14-2) + isopropylamine (75-31-0) → (S)-Atenolol (93379-54-5)

Guidance literature:

2-(4-hydroxyphenyl)acetamide; (2s)-(+)-glycidyl 3-nitrobenzenesulfonate; With potassium carbonate; cesium fluoride; In N,N-dimethyl-formamide; at 25 ℃; for 24h;

isopropylamine; at 5 ℃; for 6h;

DOI:10.1016/S0040-4020(99)00896-0

upstream raw materials:

(S)-1-phenoxy>-3-(isopropylamino)propan-2-ol

isopropylamine

(S)-2-(4-(3-chloro-2-hydroxypropoxy)phenyl)acetamide

(R)-(-)-epichlorohydrin

Downstream raw materials:

(S)-atenolol O-acetyl ester

Refernces

• 1、 Li, Jiaxi,Liu, Ruixia,Wang, Liyang,Liu, Xiaoling,Gao, Hongjie. "Enantioseparation of chiral pharmaceuticals by vancomycin-bonded stationary phase and analysis of chiral recognition mechanism". . p. 236 - 247. Retrieved 2019/02/01.
• 2、 Kucerova, Gabriela,Kalikova, Kveta,Tesarova, Eva. "Enantioselective potential of polysaccharide-based chiral stationary phases in supercritical fluid chromatography". supporting information. p. 239 - 246. Retrieved 2017/05/29.