3-{4-[2-Hydroxy-3-(propan-2-ylamino)propoxy]phenyl}propanoic acid

Base Information

• Chemical Name: 3-{4-[2-Hydroxy-3-(propan-2-ylamino)propoxy]phenyl}propanoic acid
• CAS No.: 81148-15-4
• Molecular Formula: C15H23 N O4
• Molecular Weight: 281.352
• UNII: G0SM48N856
• DSSTox Substance ID: DTXSID801001809
• Nikkaji Number: J413.176B
• Wikidata: Q27225688
• Metabolomics Workbench ID: 66906
• ChEMBL ID: CHEMBL767
• Mol file: 81148-15-4.mol

Synonyms:ALS 8123;ALS-8123

Chemical Property of 3-{4-[2-Hydroxy-3-(propan-2-ylamino)propoxy]phenyl}propanoic acid

Chemical Property:

• Vapor Pressure: 2.92E-10mmHg at 25°C
• Boiling Point: 486.1°C at 760 mmHg
• Flash Point: 247.8°C
• PSA: 78.79000
• Density: 1.139g/cm³
• LogP: 1.83240
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 281.16270821
• Heavy Atom Count: 20
• Complexity: 275

Purity/Quality:

98%, ^*data from raw suppliers

EsmololAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)NCC(COC1=CC=C(C=C1)CCC(=O)O)O
• Uses: Esmolol Acid is the major metabolite of Esmolol (E668000), a cardioselective β-adrenergic blocker. Antiarrhythmic.

Technology Process of 3-{4-[2-Hydroxy-3-(propan-2-ylamino)propoxy]phenyl}propanoic acid

There total 4 articles about 3-{4-[2-Hydroxy-3-(propan-2-ylamino)propoxy]phenyl}propanoic acid 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: 50.0%

esmolol hydrochloride (81161-17-3) → 3-<4-<2-hydroxy-3-(isopropylamino)propoxy>phenyl>propionic acid (81148-15-4)

Guidance literature:

esmolol hydrochloride; With bis(tri-n-butyltin)oxide; In toluene; for 48h; Reflux;

With water; In toluene; for 0.25h; Reflux;

DOI:10.1080/00397911.2010.530375

Reference yield:

4-hydroxyphenylpropionic acid (501-97-3) → 3-<4-<2-hydroxy-3-(isopropylamino)propoxy>phenyl>propionic acid (81148-15-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Acidic conditions; Reflux

2.1: potassium carbonate / acetone / Reflux

3.1: methanol / Reflux

4.1: bis(tri-n-butyltin)oxide / toluene / 48 h / Reflux

4.2: 0.25 h / Reflux

With potassium carbonate; bis(tri-n-butyltin)oxide; In methanol; acetone; toluene;

DOI:10.1080/00397911.2010.530375

Reference yield:

3-(4-hydroxyphenyl)propionic acid methyl ester (5597-50-2) → 3-<4-<2-hydroxy-3-(isopropylamino)propoxy>phenyl>propionic acid (81148-15-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate / acetone / Reflux

2.1: methanol / Reflux

3.1: bis(tri-n-butyltin)oxide / toluene / 48 h / Reflux

3.2: 0.25 h / Reflux

With potassium carbonate; bis(tri-n-butyltin)oxide; In methanol; acetone; toluene;

DOI:10.1080/00397911.2010.530375

upstream raw materials:

esmolol hydrochloride

4-hydroxyphenylpropionic acid

3-(4-hydroxyphenyl)propionic acid methyl ester

methyl 3-<4-(2,3-epoxypropoxy)phenyl>propionate

Downstream raw materials:

3-<4-<2-hydroxy-3-(isopropylamino)propoxy>phenyl>propionic acid hydrochloride

Refernces

• 1、 -. "MULTI-DOSE CONCENTRATE ESMOLOL WITH BENZYL ALCOHOL". Page/Page column 2-3. . Retrieved 2009/01/20.