81148-15-4

Basic information

• Product Name: ALS 8123
• Synonyms: ALS 8123;4-(2-Hydroxy-3-((1-Methylethyl )amino)Propoxy)benzenepropanoic Acid;3-[4-[2-Hydroxy-3-(isopropylamino)propoxy]phenyl]propanoic acid;4-[2-Hydroxy-3-(isopropylamino)propoxy]benzenepropanoic acid;ASL-8123;3-{4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl}propanoic acid
• CAS NO: 81148-15-4
• Molecular Formula: C₁₅H₂₃NO₄
• Molecular Weight: 281.3474
• Mol File: 81148-15-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 486.1°C at 760 mmHg
• Flash Point: 247.8°C
• Appearance: /
• Density: 1.139g/cm³
• Vapor Pressure: 2.92E-10mmHg at 25°C
• Refractive Index: 1.534
• CAS DataBase Reference: ALS 8123(CAS DataBase Reference)
• NIST Chemistry Reference: ALS 8123(81148-15-4)
• EPA Substance Registry System: ALS 8123(81148-15-4)

Safety Data

• Hazardous Substances Data: 81148-15-4(Hazardous Substances Data)

Usage

Uses

Esmolol Acid is the major metabolite of Esmolol (E668000), a cardioselective β-adrenergic blocker. Antiarrhythmic.

Definition

ChEBI: A carboxylic acid that is 3-phenylpropanoic acid substituted at position 4 by a 2-hydroxy-3-(propan-2-ylamino)propoxy group.

InChI:InChI=1/C15H23NO4/c1-11(2)16-9-13(17)10-20-14-6-3-12(4-7-14)5-8-15(18)19/h3-4,6-7,11,13,16-17H,5,8-10H2,1-2H3,(H,18,19)

Synthetic route

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

Conditions	Yield
Stage #1: esmolol hydrochloride With bis(tri-n-butyltin)oxide In toluene for 48h; Reflux; Stage #2: With water In toluene for 0.25h; Reflux;	50%
With sodium hydroxide at 100℃; for 16h;
With water at 55℃; for 168 - 672h; pH=2.24 - 3.86; Reactivity;
With water In benzyl alcohol at 55℃; for 168 - 672h; pH=2.24 - 3.89; Reactivity;
With water In benzyl alcohol at 55℃; for 168 - 672h; pH=4.6; Reactivity; Buffer;

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

Conditions	Yield
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 View Scheme

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

Conditions	Yield
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 View Scheme

methyl 3-<4-(2,3-epoxypropoxy)phenyl>propionate (81147-94-6) → 3-<4-<2-hydroxy-3-(isopropylamino)propoxy>phenyl>propionic acid (81148-15-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: methanol / Reflux 2.1: bis(tri-n-butyltin)oxide / toluene / 48 h / Reflux 2.2: 0.25 h / Reflux View Scheme

3-<4-<2-hydroxy-3-(isopropylamino)propoxy>phenyl>propionic acid (81148-15-4) → 3-<4-<2-hydroxy-3-(isopropylamino)propoxy>phenyl>propionic acid hydrochloride (83356-60-9)

Conditions	Yield
With hydrogenchloride In methanol

Upstream product

• 81161-17-3 esmolol hydrochloride 
• 81147-94-6 methyl 3-<4-(2,3-epoxypropoxy)phenyl>propionate 
• 5597-50-2 3-(4-hydroxyphenyl)propionic acid methyl ester 
• 501-97-3 4-hydroxyphenylpropionic acid 

Downstream Products

• 83356-60-9 3-<4-<2-hydroxy-3-(isopropylamino)propoxy>phenyl>propionic acid hydrochloride 

Relevant articles and documents

Hitting a soft drug with a hard nucleophile: Preparation of esmolol's metabolite by treatment with bis(tributyltin) oxide

A facile method for the production of esmolol's metabolite in high purity is described. Bis(tributyltin) oxide is used to disrupt esmolol's ester linkage, and hydrolysis is completed by addition of water, which also allows the inorganic side products to be conveniently extracted into ether. Evaporation of the aqueous phase and trituration with ethyl acetate provides the carboxylic acid-amine internal salt as a white, free-flowing powder. Taylor & Francis Group, LLC.

Ultra-Short-Acting β-Adrenergic Receptor Blocking Agents. 2. (Aryloxy)propanolamines Containing Esters on the Aryl Function

Several short-acting β-adrenergic receptor blocking agents have been prepared by incorporating ester functions into the aryl portion of certain (aryloxy)propanolamine systems.In particular, methyl 3-phenyl>propionate hydrochloride (ASL-8052) was found to be a moderately potent, cardioselective compound with a short duration of action when determined in in vivo canine models.