Pentane-1,5-diyl bis{3-[(1R)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl]propanoate}

Base Information

• Chemical Name: Pentane-1,5-diyl bis{3-[(1R)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl]propanoate}
• CAS No.: 64228-84-8
• Molecular Formula: C51H66N2O12
• Molecular Weight: 899.091
• European Community (EC) Number: 613-515-6
• UNII: ZZV7VAV7QX
• DSSTox Substance ID: DTXSID20708213
• Wikidata: Q82642383
• Mol file: 64228-84-8.mol

Synonyms:64228-84-8;ZZV7VAV7QX;UNII-ZZV7VAV7QX;(R,R)-N,N'-Didemethyl atracurium;2(1H)-Isoquinolinepropanoic acid, 1-((3,4-dimethoxyphenyl)methyl)-3,4-dihydro-6,7-dimethoxy-, 2,2'-(1,5-pentanediyl) ester, (1R,1'R)-;2,2'-(1,5-Pentanediyl) bis((1R)-1-((3,4-dimethoxyphenyl)methyl)-3,4-dihydro-6,7-dimethoxy-2(1H)-isoquinolinepropanoate);5-[3-[(1R)-1-[(3,4-Dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]propanoyloxy]pentyl 3-[(1R)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]propanoate;Pentane-1,5-diyl bis{3-[(1R)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl]propanoate};2(1H)-ISOQUINOLINEPROPANOIC ACID,1-[(3,4-DIMETHOXYPHENYL)METHYL]-3,4-DIHYDRO-6,7-DIMETHOXY-, 1,5-PENTANEDIYL ESTER, (R*,R*)-(-)-, ETHANEDIOATE;Atracurium Besylate EP impurity B;PENTANE-1,5-DIYL BIS(3-((1R)-1-((3,4-DIMETHOXYPHENYL)METHYL)-6,7-DIMETHOXY-3,4-DIHYDROISOQUINOLIN-2(1H)-YL)PROPANOATE);SCHEMBL2797941;DTXSID20708213;CISATRACURIUM BESILATE IMPURITY R [EP IMPURITY]

Chemical Property of Pentane-1,5-diyl bis{3-[(1R)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl]propanoate}

Chemical Property:

• PSA: 207.52000
• LogP: 6.80770
• XLogP3: 7.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 26
• Exact Mass: 898.46157554
• Heavy Atom Count: 65
• Complexity: 1290

Purity/Quality:

95%+ or 98%+ ^*data from raw suppliers

(R',R')-(-)-1-[(3,4-DIMETHOXYPHENYL)METHYL]-3,4-DIHYDRO-6,7-DIMETHOXY-2(1H)-ISOQUINOLINEPROPANOIC ACID-1,5-PENTANEDIYL ESTER ETHANEDIOATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)CC2C3=CC(=C(C=C3CCN2CCC(=O)OCCCCCOC(=O)CCN4CCC5=CC(=C(C=C5C4CC6=CC(=C(C=C6)OC)OC)OC)OC)OC)OC)OC
• Isomeric SMILES: COC1=C(C=C(C=C1)C[C@@H]2C3=CC(=C(C=C3CCN2CCC(=O)OCCCCCOC(=O)CCN4CCC5=CC(=C(C=C5[C@H]4CC6=CC(=C(C=C6)OC)OC)OC)OC)OC)OC)OC
• Uses: (R,R)-N,N''-Didemethyl Atracurium is a derivative and an impurity of Atricurium (A794500), a neuromuscular blocking agent.

Technology Process of Pentane-1,5-diyl bis{3-[(1R)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl]propanoate}

There total 5 articles about Pentane-1,5-diyl bis{3-[(1R)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl]propanoate} 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: 90.8%

1 ,5-pentanediol (111-29-5) + C23H29NO6 → N,N'-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis-(R)-(-)-tetrahydropapaverine (64228-84-8)

Guidance literature:

With cobalt(II) chloride hexahydrate; acetic acid; In acetonitrile; at 60 ℃; for 12h;

Reference yield:

pentamethylene 1,5-diacrylate (36840-85-4) + (-) N-norlaudanosine (50896-90-7) → N,N'-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis-(R)-(-)-tetrahydropapaverine (64228-84-8)

Guidance literature:

With acetic acid; at 70 ℃; for 4h; Yield given;

Reference yield:

1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-3.4-dihydroisoquinoline hydrochloride (5884-22-0) → N,N'-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis-(R)-(-)-tetrahydropapaverine (64228-84-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium tetrahydroborate; zinc(II) chloride; (2S,3S)-1-methyl-5-oxo-2-phenyltetrahydro-1H-pyrrolidine-3-carboxylic acid / tetrahydrofuran / 21 h / 20 °C / Inert atmosphere; Reflux

2.1: acetic acid / toluene / 4 h / 80 °C

2.2: 1 h / 20 °C

3.1: sodium hydroxide / water; dichloromethane / 0.25 h / 20 °C / pH 9 - 10

3.2: 2 h / 8 - 12 °C / 760.05 Torr

4.1: acetic acid; cobalt(II) chloride hexahydrate / acetonitrile / 12 h / 60 °C

With sodium tetrahydroborate; (2S,3S)-1-methyl-5-oxo-2-phenyltetrahydro-1H-pyrrolidine-3-carboxylic acid; cobalt(II) chloride hexahydrate; acetic acid; sodium hydroxide; zinc(II) chloride; In tetrahydrofuran; dichloromethane; water; toluene; acetonitrile;

upstream raw materials:

pentamethylene 1,5-diacrylate

(-) N-norlaudanosine

1 ,5-pentanediol

1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-3.4-dihydroisoquinoline hydrochloride

Downstream raw materials:

cisatracurium besylate