(1R,1'R)-2,2'-(3,11-Dioxo-4,10-dioxatridecamethylene)-bis-(1,2,3,4-tetrahydro-6,7-dimethoxy-1-veratrylisoquindline)-dioxalate

Base Information

• Chemical Name: (1R,1'R)-2,2'-(3,11-Dioxo-4,10-dioxatridecamethylene)-bis-(1,2,3,4-tetrahydro-6,7-dimethoxy-1-veratrylisoquindline)-dioxalate
• CAS No.: 96687-52-4
• Molecular Formula: 2C₂H₂O₄*C₅₁H₆₆N₂O₁₂
• Molecular Weight: 1079.16
• Mol file: 96687-52-4.mol

Synonyms:(1R,1R)-2,2-(3,11-Dioxo-4,10-dioxatridecamethylene)-bis-(1,2,3,4-tetrahydro-6,7-dimethoxy-1-veratrylisoquindline)-dioxalate;Intermediate of Cisatracurium Besylate;Maleicbenzeneakumaamine atracurium intermediates;

Chemical Property of (1R,1'R)-2,2'-(3,11-Dioxo-4,10-dioxatridecamethylene)-bis-(1,2,3,4-tetrahydro-6,7-dimethoxy-1-veratrylisoquindline)-dioxalate

Chemical Property:

• Boiling Point: 916.8 °C at 760 mmHg
• Flash Point: 508.3 °C
• PSA: 282.12000
• LogP: 5.96330
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

99% ^*data from raw suppliers

(R,R)-N,N''-DidemethylAtracuriumOxalate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (R,R)-N,N'-Didemethyl Atracurium Oxalate is a derivative of Atricurium, a neuromuscular blocking agent. UV stabilizer (R,R)-N,N''-Didemethyl Atracurium Oxalate is a derivative of Atricurium (A794500), a neuromuscular blocking agent.

Technology Process of (1R,1'R)-2,2'-(3,11-Dioxo-4,10-dioxatridecamethylene)-bis-(1,2,3,4-tetrahydro-6,7-dimethoxy-1-veratrylisoquindline)-dioxalate

There total 10 articles about (1R,1'R)-2,2'-(3,11-Dioxo-4,10-dioxatridecamethylene)-bis-(1,2,3,4-tetrahydro-6,7-dimethoxy-1-veratrylisoquindline)-dioxalate 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: 86.0%

1 ,5-pentanediol (111-29-5) + (1R)-1-[(3,4-dimethoxyphenyl)-methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-tert-butoxycarbonylethyl-isoquinoline oxalate (1075726-71-4) + oxalic acid (144-62-7,97993-78-7) → N,N'-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis-(R)-(-)-tetrahydropapaverine dioxalate (64228-78-0,64493-10-3,83285-74-9,96687-52-4,96687-53-5,110817-20-4)

Guidance literature:

(1R)-1-[(3,4-dimethoxyphenyl)-methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-tert-butoxycarbonylethyl-isoquinoline oxalate; With ammonium hydroxide; In water; for 0.5h;

With toluene-4-sulfonic acid; at 50 - 55 ℃; for 4.5h;

1 ,5-pentanediol; oxalic acid; Further stages;

Reference yield: 51.0%

pentamethylene 1,5-diacrylate (36840-85-4) + 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5,66820-84-6) → pentamethylene bis(1-(3,4-dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxy-1H-isoquinoline-2-propionate) dioxalate (64228-78-0,64493-10-3,83285-74-9,96687-52-4,96687-53-5,110817-20-4)

Guidance literature:

In benzene; for 48h; Heating;

Reference yield:

pentamethylene 1,5-diacrylate (36840-85-4) + (R)-tetrahydropapaverine-N-acetyl-D-leucine salt (876290-45-8,141109-12-8) + oxalic acid (144-62-7,97993-78-7) + acetic anhydride (108-24-7) → N,N'-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis-(R)-(-)-tetrahydropapaverine dioxalate (64228-78-0,64493-10-3,83285-74-9,96687-52-4,96687-53-5,110817-20-4) + (R)-2-Acetyl-1-<(3,4-dimethoxyphenyl)methyl>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (860-24-2,860-23-1)

Guidance literature:

(R)-tetrahydropapaverine-N-acetyl-D-leucine salt; With ammonia; In dichloromethane; water;

pentamethylene 1,5-diacrylate; With acetic acid; at 70 - 75 ℃; Inert atmosphere;

oxalic acid; acetic anhydride;

upstream raw materials:

pentamethylene 1,5-diacrylate

1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride

(3,4-Dimethoxyphenyl)acetic acid

N-(3,4-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide

Downstream raw materials:

C₅₃H₇₂N₂O₁₂⁽²⁺⁾*2CH₃O₃S^(1-)

3-[1-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionic acid 2-{3-[1-(3,4-dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionyloxy}-ethyl ester; compound with oxalic acid

atracurium besylate

cisatracurium besylate

Refernces

• 1、 -. "AN IMPROVED PROCESS FOR THE PREPARATION OF TETRAHYDROISOQUINOLINE COMPOUNDS". Page/Page column 25. . Retrieved 2018/11/22.
• 2、 Stenlake,Waigh,Dewar,et al.. "Biodegradable neuromuscular blocking agents. Part 4. Atracurium besylate and related polyalkylene di-esters". . p. 515 - 524. Retrieved 2007/10/02.