Beraprost sodium salt

Base Information

• Chemical Name: Beraprost sodium salt
• CAS No.: 88475-69-8
• Molecular Formula: C24H29NaO5
• Molecular Weight: 398.499
• European Community (EC) Number: 685-277-1
• NCI Thesaurus Code: C79991
• Mol file: 88475-69-8.mol

Synonyms:4-(1,2,3a,8b-tetrahydro-2-hydroxy-1-(3-hydroxy-4-methyloct-6-yne-1-enyl)-5-cyclopenta(b)benzofuranyl)butyrate;beraprost;beraprost sodium;TRK 100;TRK-100

Chemical Property of Beraprost sodium salt

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 6.32E-14mmHg at 25°C
• Melting Point: 204-206 °C
• Boiling Point: 572.1 °C at 760 mmHg
• Flash Point: 193.1 °C
• PSA: 89.82000
• LogP: 1.95120
• Storage Temp.: Amber Vial, -20?C Freezer, Under Inert Atmosphere
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 420.19126830
• Heavy Atom Count: 30
• Complexity: 665

Purity/Quality:

98.5%-101.0% ^*data from raw suppliers

BeraprostSodiumSalt ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC#CCC(C)C(C=CC1C(CC2C1C3=CC=CC(=C3O2)CCCC(=O)[O-])O)O.[Na+]
• Isomeric SMILES: CC#CCC(C)[C@@H](/C=C/C1[C@@H](C[C@H]2[C@@H]1C3=CC=CC(=C3O2)CCCC(=O)[O-])O)O.[Na+]
• Recent ClinicalTrials: Protective Effect of Beraprost Sodium Tablets on Reperfusion Therapy for Acute STEMI
• Recent EU Clinical Trials: A 12-week, double-blind, international, multicenter, dose-response study of the safety and efficacy of Beraprost Sodium Modified Release (BPS-MR) in patients with pulmonary arterial hypertension (PAH)
• Description: Beraprost sodium is a new, orally active antithrombotic epoprostenol analog introduced as a treatment for peripheral vascular disease, including Raynaud's syndrome and Buerger's disease. The antiplatelet activity may be due to its elevation of cyclic AMP in platelets which is achieved by activating adenylate cyclase in the platelet membrane, followed by the inhibition ofCa++- influx and thromboxane A2 formation. Beraprost is an analog of prostacyclin in which the unstable enol-ether has been replaced by a benzofuran ether function. This modification increases the plasma half-life from 30 seconds to several hours, and permits the compound to be taken orally. Doses of 20-100 μg in humans, given 1 to 3 times per day, have been demonstrated to improve clinical end points in diseases responsive to prostacyclin. Oral beraprost therapy improved the survival and pulmonary hemodynamics of patients with primary pulmonary hypertension. Beraprost inhibits platelet aggregation in healthy subjects and in diabetic patients at similar doses.

Technology Process of Beraprost sodium salt

There total 12 articles about Beraprost sodium salt 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: 92.3%

C25H32O5 → beraprost (88475-69-8,88430-50-6)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 30 - 35 ℃; Solvent;

Reference yield:

methyl 4-((1S,2R,3aS,8bS)-2-hydroxy-1-(hydroxymethyl)-2,3,3a,8b-tetrahydro-1Hbenzo[b]cyclopenta[d]furan-5-yl)butanoate (88277-19-4,132203-90-8) → beraprost (88475-69-8,88430-50-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / N,N-dimethyl acetamide; dichloromethane / 5 h / 30 - 35 °C

2.1: sodium hydride / tetrahydrofuran / 1 h / 0 - 5 °C

2.2: 6 h / 25 - 35 °C

3.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate; methanol / methanol / 0.17 h / 10 °C

4.1: sodium hydroxide / tetrahydrofuran / 30 - 35 °C

With methanol; sodium tetrahydroborate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; cerium(III) chloride heptahydrate; sodium hydride; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl acetamide;

Reference yield:

4-((1S,2R,3aS,8bS)-2-Acetoxy-1-hydroxymethyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl)-butyric acid methyl ester (88295-11-8) → beraprost (88475-69-8,88430-50-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine; trifluoroacetic acid; dicyclohexyl-carbodiimide / benzene; dimethyl sulfoxide / 14 h / 20 °C

2.1: sodium hydroxide / 1,2-dimethoxyethane / 0.5 h / 20 °C

2.2: 0.5 h / 20 °C

3.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate; methanol / 0.17 h / 10 °C

3.2: 7.5 h

4.1: sodium hydroxide / tetrahydrofuran / 30 - 35 °C

With pyridine; methanol; sodium tetrahydroborate; cerium(III) chloride heptahydrate; dicyclohexyl-carbodiimide; trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; 1,2-dimethoxyethane; dimethyl sulfoxide; benzene;

upstream raw materials:

methyl 4-((1S,2R,3aS,8bS)-2-hydroxy-1-(hydroxymethyl)-2,3,3a,8b-tetrahydro-1Hbenzo[b]cyclopenta[d]furan-5-yl)butanoate

4-((1S,2R,3aS,8bS)-2-Acetoxy-1-hydroxymethyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl)-butyric acid methyl ester

4-((1R,2R,3aS,8bS)-2-Acetoxy-1-formyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl)-butyric acid methyl ester

dimethyl (2-oxo-3-methylhept-5-ynyl)-phosphonate

Refernces

• 1、 -. "THERAPY FOR COMPLICATIONS OF DIABETES". . . Retrieved 2009/07/02.
• 2、 -. "Method for treating resistant hypertension". . . Retrieved 2008/06/13.