(R)-(+)-Ropivacaine

Base Information

• Chemical Name: (R)-(+)-Ropivacaine
• CAS No.: 98717-16-9
• Molecular Formula: C₁₇H₂₆N₂O
• Molecular Weight: 274.406
• UNII: 0494L275Q6
• DSSTox Substance ID: DTXSID701317045
• Nikkaji Number: J984.845B
• Wikidata: Q27247635
• ChEMBL ID: CHEMBL4564685
• Mol file: 98717-16-9.mol

Synonyms:98717-16-9;(R)-(+)-Ropivacaine;(R)-N-(2,6-Dimethylphenyl)-1-propylpiperidine-2-carboxamide;Ropivacaine, (R)-;(R)-ropivacaine;CHEMBL4564685;(2R)-N-(2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide;UNII-0494L275Q6;(+)-(2R)-N-(2,6-Dimethylphenyl)-1-propylpiperidine-2-carboxamide;2-Piperidinecarboxamide, N-(2,6-dimethylphenyl)-1-propyl-, (2R)-;0494L275Q6;Ropivacaine hydrochloride monohydrate specified impurity G [EP];(+)-Ropivacaine;SCHEMBL33293;DTXSID701317045;BDBM50505291;BS-18064;LS-114556;CS-0163000;C77370;A922718;Q27247635;2-Piperidinecarboxamide, N-(2,6-dimethylphenyl)-1-propyl-(R)-;ROPIVACAINE HYDROCHLORIDE MONOHYDRATE IMPURITY G [EP IMPURITY]

Chemical Property of (R)-(+)-Ropivacaine

Chemical Property:

• Boiling Point: 410.2±45.0 °C(Predicted)
• PKA: 14.85±0.70(Predicted)
• PSA: 35.83000
• Density: 1.044±0.06 g/cm3(Predicted)
• LogP: 4.09380
• Storage Temp.: 2-8°C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 274.204513457
• Heavy Atom Count: 20
• Complexity: 308

Purity/Quality:

99% ^*data from raw suppliers

Ropivacaine impurity G European Pharmacopoeia (EP) Reference Standard ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Human systemic effects
• Hazard Codes: Human systemic effects

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCN1CCCCC1C(=O)NC2=C(C=CC=C2C)C
• Isomeric SMILES: CCCN1CCCC[C@@H]1C(=O)NC2=C(C=CC=C2C)C

Technology Process of (R)-(+)-Ropivacaine

There total 23 articles about (R)-(+)-Ropivacaine 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: 99.0%

propan-1-ol (71-23-8) + (R)-2',6'-pipecoloxylidide → (+)-Ropivacaine (98717-16-9)

Guidance literature:

With diphenyl hydrogen phosphate; 1-hydroxytetraphenyl-cyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II); In neat (no solvent); at 90 ℃; for 24h; stereoselective reaction;

DOI:10.1002/cssc.202100373

Reference yield: 95.0%

2',6'-pipecoloxylidide (15883-20-2,27262-40-4,27262-43-7,78341-12-5) + propyl bromide (106-94-5) → 1-propyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide (98626-61-0,98717-16-9)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 78 ℃; for 2h; Temperature;

Reference yield: 94.0%

propyl bromide (106-94-5) + (S)-2',6'-pipecoloxylidide (27262-40-4) → ropivacaine (84057-95-4,98717-16-9)

Guidance literature:

In tetrahydrofuran; for 20 - 24h; Heating / reflux;

upstream raw materials:

propyl bromide

ropivacaine

pipecolic Acid

2',6'-pipecoloxylidide

Downstream raw materials:

ropivacaine

Refernces

• 1、 Yang, Yuyan,Li, Hua,You, Zhonglin,Zhang, Xingxian. "A convenient and highly enantioselective synthesis of (S)-2-pipecolic acid: an efficient access to caine anesthetics". . p. 3084 - 3089. Retrieved 2021/08/12.
• 2、 Yan, Tao,Feringa, Ben L.,Barta, Katalin. "Direct Catalytic N-Alkylation of α-Amino Acid Esters and Amides Using Alcohols with High Retention of Stereochemistry". . p. 2303 - 2307. Retrieved 2021/05/11.