Benzenepropanoic acid,4-[(2S)-2-hydroxy-3-[[2-[(4-morpholinylcarbonyl)amino]ethyl]amino]propoxy]-,[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl ester, hydrochloride (1:1)

Base Information

• Chemical Name: Benzenepropanoic acid,4-[(2S)-2-hydroxy-3-[[2-[(4-morpholinylcarbonyl)amino]ethyl]amino]propoxy]-,[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl ester, hydrochloride (1:1)
• CAS No.: 144481-98-1
• Molecular Formula: C25H39N3O8^.HCl
• Molecular Weight: 546.061
• European Community (EC) Number: 833-743-1
• UNII: G8HQ634Y17
• DSSTox Substance ID: DTXSID3048605
• Wikidata: Q27278937
• NCI Thesaurus Code: C190448
• ChEMBL ID: CHEMBL2362410
• Mol file: 144481-98-1.mol

Synonyms:Benzenepropanoicacid,4-[(2S)-2-hydroxy-3-[[2-[(4-morpholinylcarbonyl)amino]ethyl]amino]propoxy]-,[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl ester, monohydrochloride (9CI);Benzenepropanoic acid, 4-[2-hydroxy-3-[[2-[(4-morpholinylcarbonyl)amino]ethyl]amino]propoxy]-,(2,2-dimethyl-1,3-dioxolan-4-yl)methyl ester, monohydrochloride, [S-(R*,R*)]-;ONO 1101 hydrochloride;Onoact;

Chemical Property of Benzenepropanoic acid,4-[(2S)-2-hydroxy-3-[[2-[(4-morpholinylcarbonyl)amino]ethyl]amino]propoxy]-,[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl ester, hydrochloride (1:1)

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 3.24E-22mmHg at 25°C
• Melting Point: 122-127oC
• Boiling Point: 727.5 °C at 760 mmHg
• Flash Point: 393.8 °C
• PSA: 127.82000
• Density: 1.201g/cm3
• LogP: 2.37760
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Ethanol (Slightly, Sonicated)
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 14
• Exact Mass: 545.2503929
• Heavy Atom Count: 37
• Complexity: 666

Purity/Quality:

99% ^*data from raw suppliers

Landiolol Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OCC(O1)COC(=O)CCC2=CC=C(C=C2)OCC(CNCCNC(=O)N3CCOCC3)O)C.Cl
• Isomeric SMILES: CC1(OC[C@H](O1)COC(=O)CCC2=CC=C(C=C2)OC[C@H](CNCCNC(=O)N3CCOCC3)O)C.Cl
• Recent ClinicalTrials: Landiolol for Prevention of Postoperative Atrial Fibrillation in Patients Undergoing Cardiac Surgery
• Recent EU Clinical Trials: A prospective, randomized, double- blind, placebo- controlled study to evaluate the efficacy of Landiolol hydrochloride for prevention of atrial fibrillation in patients undergoing cardiac surgery
• Recent NIPH Clinical Trials: A study of efficacy and safety of landiolol hydrochloride for pulmonary resection
• Description: Landiolol hydrochloride (14) was launched in Japan by Ono for the treatment of intraoperative tachyarrhythmia. It improves tachyarrhythmia by selectively blocking β1 receptors located mainly in the heart and by inhibiting the action of catecholamine.
• Uses: Landiolol is an ultra-short acting beta blocker that is used to treat patients with cardiac arrhythmias and is also used to treat tachycardia during anasthesia.

Technology Process of Benzenepropanoic acid,4-[(2S)-2-hydroxy-3-[[2-[(4-morpholinylcarbonyl)amino]ethyl]amino]propoxy]-,[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl ester, hydrochloride (1:1)

There total 10 articles about Benzenepropanoic acid,4-[(2S)-2-hydroxy-3-[[2-[(4-morpholinylcarbonyl)amino]ethyl]amino]propoxy]-,[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl ester, hydrochloride (1:1) 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: 95.9%

2,2-dimethyl-1,3-dioxolan-4S-ylmethyl 3-<4-<3-<2-(morpholinocarbonylamino)ethylamino>-2S-hydroxypropoxy>phenyl>propionate (133242-30-5) → Landiolol hydrochloride (144481-98-1,1253907-79-7)

Guidance literature:

With hydrogenchloride; In ethyl acetate; at 5 - 10 ℃; for 2h;

Reference yield: 85.2%

[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl-3-{4-[(2S)-2-hydroxy-3-[(2-{[(morpholin-4-yl)carbonyl]amino}ethyl)amino]propoxy]phenyl}propanoate oxalate → Landiolol hydrochloride (144481-98-1,1253907-79-7)

Guidance literature:

With pyridine hydrochloride; sodium hydroxide; In water; isopropyl alcohol; at 0 - 50 ℃; for 16h; pH=8.5; Solvent; Reagent/catalyst; Temperature;

Reference yield: 78.4%

N-(2-aminoethyl)-4-morpholine carboxamide oxalic acid (154467-16-0,947674-94-4) + [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 3-{4-[(2S)-2-hydroxypropoxy]phenyl}propanoate → Landiolol hydrochloride (144481-98-1,1253907-79-7)

Guidance literature:

N-(2-aminoethyl)-4-morpholine carboxamide oxalic acid; [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 3-{4-[(2S)-2-hydroxypropoxy]phenyl}propanoate; With sodium hydroxide; In water; isopropyl alcohol; at 30 - 40 ℃; for 8h; pH=9;

With hydrogenchloride; In ethyl acetate; pH=4 - 4.5;

upstream raw materials:

3-(4-hydroxyphenyl)propionic acid [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl ester

2-(morpholine-4-carboxamido)ethanamino hydrochloride

2,2-dimethyl-1,3-dioxolan-4S-ylmethyl 3-<4-<3-<2-(morpholinocarbonylamino)ethylamino>-2S-hydroxypropoxy>phenyl>propionate

N-(2-aminoethyl)-4-morpholine carboxamide oxalic acid

Refernces

• 1、 -. "Preparation method of landiolol hydrochloride intermediate". Paragraph 0026. . Retrieved 2021/06/06.
• 2、 -. "Process for the enantioselective synthesis of landiolol". . . Retrieved 2018/06/28.