2-(2-carboxyethyl)-1-[(3,4-dimethoxyphenyl)methyl]-,1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-isoquinolinium benzenesulfonate

Base Information

• Chemical Name: 2-(2-carboxyethyl)-1-[(3,4-dimethoxyphenyl)methyl]-,1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-isoquinolinium benzenesulfonate
• CAS No.: 1075727-06-8
• Molecular Formula: C24H32NO6 . C6H5O3S
• Molecular Weight: 587.691
• Mol file: 1075727-06-8.mol

Synonyms:(1R,2R)-2-(2-carboxyethyl)-;AtracuriuM Besylate iMpurity A;Atracurium Impurity D Besylate;Cisatracurium EP Impurity A Besylate;Cisatracurium Besylate EP Impurity A;Cisatracurium Besilate EP Impurity A Iodide;Cisatracurium Besylate EP Impurity A(Besylate);(R-cis-N-Methyl-N-Alkyl-(Acid)-tetrahydropapaverine) besylate;Atracurium Impurity 4 Iodide（Cisatracurium Besilate EP Impurity A Iodide）;(1R,2R)-2-(2-Carboxyethyl)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoqu

Chemical Property of 2-(2-carboxyethyl)-1-[(3,4-dimethoxyphenyl)methyl]-,1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-isoquinolinium benzenesulfonate

Chemical Property:

• PSA: 139.80000
• LogP: 5.11250

Purity/Quality:

99% ^*data from raw suppliers

(1R,2R)-2-(2-Carboxyethyl)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-2-iumbenzenesulfonate 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (R)-Laudanosine N-Carboxyethyl Benzenesulfonate is an impurity of Cisatracurium (C496700), an enantiomer of a neuromuscular blocking agent. It could be used in liver transplant patient with safety.

Technology Process of 2-(2-carboxyethyl)-1-[(3,4-dimethoxyphenyl)methyl]-,1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-isoquinolinium benzenesulfonate

There total 6 articles about 2-(2-carboxyethyl)-1-[(3,4-dimethoxyphenyl)methyl]-,1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-isoquinolinium benzenesulfonate 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: 100.0%

(1R-cis)-1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-2-tert-butoxycarbonylethyl-isoquinolinium besylate (1075727-00-2) → (1R,2R)-2-(2-carboxyethyl)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolinium besylate (1075727-06-8)

Guidance literature:

With trifluoroacetic acid; at 0 - 5 ℃; for 0.333333h; Product distribution / selectivity;

Reference yield: 92.0%

(1R-cis)-1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-2-benzyloxycarbonylethyl-isoquinolinium besylate (1075726-96-3) → (1R,2R)-2-(2-carboxyethyl)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolinium besylate (1075727-06-8)

Guidance literature:

With hydrogen; 5%-palladium/activated carbon; In methanol; at 10 ℃; for 2h; Product distribution / selectivity;

Reference yield:

C23H29NO6 + Methyl benzenesulfonate (80-18-2) → (1R,2R)-2-(2-carboxyethyl)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolinium besylate (1075727-06-8)

Guidance literature:

In acetonitrile; at 25 ℃; for 24h; Temperature;

upstream raw materials:

(1R-cis)-1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-2-benzyloxycarbonylethyl-isoquinolinium besylate

(1R-cis)-1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-2-tert-butoxycarbonylethyl-isoquinolinium besylate

1 ,5-pentanediol

Methyl benzenesulfonate

Downstream raw materials:

cis-(R)-1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-2-[3-[(5-hydroxypentyl)oxy]-3-oxopropyl]-6,7-dimethoxy-2-methyl-isoquinolinium besylate

C₆H₅O₃S^(1-)*C₂₄H₃₁ClNO₅⁽¹⁺⁾

Refernces

• 1、 -. "PROCESS FOR PRODUCING CISATRACURIUM AND ASSOCIATED INTERMEDIATES". Page/Page column 17. . Retrieved 2009/03/07.
• 2、 -. "NOVEL ISOQUINOLINIUM COMPOUNDS USEFUL IN THE PREPARATION OF CISATRACURIUM AND ASSOCIATED INTERMEDIATES". Page/Page column 39. . Retrieved 2008/12/08.