136310-64-0

Basic information

• Product Name: Scopine-2,2-dithienyl glycolate
• Synonyms: SCOPINE-2,2-DITHIENYL GLYCOLATE;2-thiopheneacetic acid, a-hydroxy-a-2th ( Di(2-thienyl) Glycolate );N-DeMethyl TiotropiuM;α-Hydroxy-α-2-thienyl-2-thiopheneacetic Acid (1α,2β,4β,5α,7β)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl Ester;Scopine di(2-thienyl)glycolate scopine-2-dithienyl glycolate;Tiotropium EP Impurity B;2-Thiopheneacetic acid, -hydroxy--2-thienyl-, (1,2,4,5,7);(1R,2R,4S,5S,7s)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl 2-hydroxy-2,2-dithiophen-2-ylacetate
• CAS NO: 136310-64-0
• Molecular Formula: C₁₈H₁₉NO₄S₂
• Molecular Weight: 377.483
• EINECS: 1533716-785-6
• Product Categories: TIOTROPIUM BROMIDE;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Tiotropium Bromide Intermediates
• Mol File: 136310-64-0.mol
• Article Data: 19

Chemical Properties

• Melting Point: 138-140°C
• Boiling Point: 542.3 ºC at 760 mmHg
• Flash Point: 281.7 ºC
• Appearance: /
• Density: 1.48 g/cm³
• Vapor Pressure: 1.37E-12mmHg at 25°C
• Refractive Index: 1.687
• Storage Temp.: -20°C Freezer
• PKA: 10.32±0.29(Predicted)
• CAS DataBase Reference: Scopine-2,2-dithienyl glycolate(CAS DataBase Reference)
• NIST Chemistry Reference: Scopine-2,2-dithienyl glycolate(136310-64-0)
• EPA Substance Registry System: Scopine-2,2-dithienyl glycolate(136310-64-0)

Safety Data

• Hazardous Substances Data: 136310-64-0(Hazardous Substances Data)

Usage

Description

Scopine-2,2-dithienyl glycolate, also known as Scopine Di(2-thienylglycolate) or Tiotropium EP Impurity B, is an organic compound that serves as a crucial intermediate in the synthesis of tiotropium bromide. It is characterized by its off-white solid appearance and a melting point of 138-140°C. The compound is stored at a temperature of -20°C to maintain its stability and integrity.

Uses

Scopine-2,2-dithienyl glycolate is primarily used as a precursor in the pharmaceutical industry for the production of tiotropium bromide, a highly effective anticholinergic agent. Tiotropium bromide is widely prescribed for the treatment of asthma and chronic obstructive pulmonary disease (COPD).
Used in Pharmaceutical Industry:
Scopine-2,2-dithienyl glycolate is used as a key intermediate for the synthesis of tiotropium bromide, which is an anticholinergic agent. The compound plays a vital role in the development of this medication due to its effectiveness in treating respiratory conditions such as asthma and COPD. Its use in the pharmaceutical industry is focused on improving the quality of life for patients suffering from these respiratory ailments by providing a more effective treatment option.

InChI:InChI=1/C18H19NO4S2/c1-19-11-8-10(9-12(19)16-15(11)23-16)22-17(20)18(21,13-4-2-6-24-13)14-5-3-7-25-14/h2-7,10-12,15-16,21H,8-9H2,1H3

Upstream product

• 26447-85-8 hydroxy-di-thiophen-2-yl-acetic acid methyl ester 
• 85700-55-6 6exo,7exo-epoxy-tropane-3endo-ol; scopine; hydrochloride 
• 51-34-3 scopolamine 
• 22143-95-9 tropenol 
• 1003-09-4 2-bromothiophene 
• 498-45-3 scopine 
• 1454836-37-3 C₁₀H₁₂ClNO₄ 
• 5713-61-1 thiophen-2-yl magnesium bromide 
• 1449372-70-6 (1α,2β,4β,5α,7β)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0^2,4]nonan-7-ol oxalate 
• 672-21-9 (+/-)-Scopolamine hydrobromide 
• 20513-09-1 (1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-ol 
• 22150-33-0 (1R,3S,5S)-3'-hydroxy-2'-phenylpropionic acid 8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-yl ester 
• 136310-66-2 (1R,3S,5S)-2'-hydroxy-2',2'-di(thiophen-2''-yl)acetic acid 8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-yl ester 

Downstream Products

• 139404-48-1 tiotropium bromide 
• 1256081-14-7 C₁₀H₁₅O₄S^(1-)*C₁₉H₂₂NO₄S₂⁽¹⁺⁾ 

Relevant articles and documents

Crystal Structures of Tiotropium Bromide and Its Monohydrate in View of Combined Solid-state Nuclear Magnetic Resonance and Gauge-Including Projector-Augmented Wave Studies

Tiotropium bromide is an anticholinergic bronchodilator used in the management of chronic obstructive pulmonary disease. The crystal structures of this compound and its monohydrate have been previously solved and published. However, in this paper, we showed that those structures contain some major errors. Our methodology based on combination of the solid-state nuclear magnetic resonance (NMR) spectroscopy and quantum mechanical gauge-including projector-augmented wave (GIPAW) calculations of NMR shielding constants enabled us to correct those errors and obtain reliable structures of the studied compounds. It has been proved that such approach can be used not only to perform the structural analysis of a drug substance and to identify its polymorphs, but also to verify and optimize already existing crystal structures.

NMR study on (1α, 2β, 4β, 5α, 7β)-7-[(hydroxydi-2-thienylacetyl) oxy]-9,9-dimethyl-3-oxa-9-azoniatricyclo [3.3.1.02,4] nonane bromide monohydrate

The structure of (1α, 2β, 4β, 5α, 7β)-7-[(hydroxydi-2-thienylacetyl) oxy]-9,9-dimethyl-3-oxa-9-azoniatricyclo [3.3.1.02,4] nonane bromide monohydrate was studied using 1D and 2D NMR techniques. Complete NMR assignments of the compound were obtained using DEPT, H-H COSY, as well as HMQC and HMBC heteronuclear correlation techniques.

AN IMPROVED PROCESS FOR PREPARATION OF SCOPINE HYDROBROMIDE

The present invention relates to an efficient and industrially advantageous process for the preparation of scopine free base or salts. Said compounds are important intermediates in the synthesis of tiotropium and pharmaceutically acceptable salts thereof. The method provided for preparing scopine free base or its salts has the advantages of a simple operation, high yield and low costs.

A tiotropium bromide intermediate preparation method

The invention relates to a preparation method of a tiotropium bromide intermediate, that is, scopine-2,2-di(2-thienyl)glycolate. The method is characterized in that Lewis acid is used as a catalyst, and scopine and 2,2-di(2-thienyl)methyl glycolate are stirred and react with each other in an organic solvent at the temperature of 50-120 DEG C to produce the scopine-2,2-di(2-thienyl)glycolate, wherein the organic solvent is selected from one or more of non-alcohol, non-carboxylic and non-ester organic solvents.