1-[2-[(3-Methyl-1,2,3,4-tetrahydroquinoline-8-yl)sulfonylamino]-5-guanidinopentanoyl]-4-methylpiperidine-2-carboxylic acid

Base Information

• Chemical Name: 1-[2-[(3-Methyl-1,2,3,4-tetrahydroquinoline-8-yl)sulfonylamino]-5-guanidinopentanoyl]-4-methylpiperidine-2-carboxylic acid
• CAS No.: 121785-71-5
• Molecular Formula: C₂₃H₃₆N₆O₅S
• Molecular Weight: 508.642
• Hs Code.: 2935009090
• European Community (EC) Number: 687-697-0
• DSSTox Substance ID: DTXSID10860975
• Nikkaji Number: J22.668H
• Mol file: 121785-71-5.mol

Synonyms:21S-Argatroban;183679-05-2;121785-71-5;1-[2-[(3-Methyl-1,2,3,4-tetrahydroquinoline-8-yl)sulfonylamino]-5-guanidinopentanoyl]-4-methylpiperidine-2-carboxylic acid;1-[5-Carbamimidamido-2-(3-methyl-1,2,3,4-tetrahydroquinoline-8-sulfonamido)pentanoyl]-4-methylpiperidine-2-carboxylic acid;C23-H36-N6-O5-S;189264-03-7;SCHEMBL4933701;DTXSID10860975;CHEBI:182647;HMS3393N07;FT-0602870;FT-0662275;FT-0662276;FT-0662277;EN300-270191;MD-805 (monohydrate);MCI-9038 (monohydrate);Argipidine (monohydrate);1-[5-(diaminomethylideneamino)-2-[(3-methyl-1,2,3,4-tetrahydroquinolin-8-yl)sulonylamino]pentanoyl]-4-methylpiperidine-2-carboxylic acid;1-[5-Carbamimidamido-2-(3-methyl-1,2,3,4-tetrahydroquinoline-8-sulfonamido)pentanoyl]-4-methylpiperidine-2-carboxylicacid;4-Methyl-1-[N~2~-(3-methyl-1,2,3,4-tetrahydroquinoline-8-sulfonyl)arginyl]piperidine-2-carboxylic acid

Chemical Property of 1-[2-[(3-Methyl-1,2,3,4-tetrahydroquinoline-8-yl)sulfonylamino]-5-guanidinopentanoyl]-4-methylpiperidine-2-carboxylic acid

Chemical Property:

• Boiling Point: 801.3°Cat760mmHg
• PKA: 10.44±0.40(Predicted)
• Flash Point: 438.4°C
• PSA: 186.09000
• Density: 1.47g/cm³
• LogP: 3.65110
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 508.24678944
• Heavy Atom Count: 35
• Complexity: 887

Purity/Quality:

98%,99%, ^*data from raw suppliers

21R-Argatroban ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCN(C(C1)C(=O)O)C(=O)C(CCCN=C(N)N)NS(=O)(=O)C2=CC=CC3=C2NCC(C3)C
• Uses: The 21R-stereoisomer

Technology Process of 1-[2-[(3-Methyl-1,2,3,4-tetrahydroquinoline-8-yl)sulfonylamino]-5-guanidinopentanoyl]-4-methylpiperidine-2-carboxylic acid

There total 7 articles about 1-[2-[(3-Methyl-1,2,3,4-tetrahydroquinoline-8-yl)sulfonylamino]-5-guanidinopentanoyl]-4-methylpiperidine-2-carboxylic acid 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: 42.5%

argatroban → argatroban (121785-71-5) + (21R)-argatroban (121785-72-6)

Guidance literature:

In methanol; at 20 ℃; for 3 - 6h; Product distribution / selectivity; Heating / reflux; Resolution of racemate;

Reference yield:

(2R,4R)-1-(Nω′-((benzyloxy)carbonyl)-N2-((3-methylquinolin-8-yl)sulfonyl)-L-arginyl)-4-methylpiperidine-2-carboxylic acid → argatroban (121785-71-5) + (21R)-argatroban (121785-72-6)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; acetic acid; In ethanol; at 20 ℃; for 16h; under 760.051 Torr; stereoselective reaction;

DOI:10.1002/ejoc.201900399

Reference yield:

C23H31N7O7S → argatroban (121785-71-5) + (21R)-argatroban (121785-72-6)

Guidance literature:

With hydrogen; acetic acid; palladium on activated charcoal; In ethanol; Yield given. Yields of byproduct given;

DOI:10.1002/jps.2600820627

upstream raw materials:

Boc-Arg(Z)2-OH

Refernces

• 1、 van der Heijden, Gydo,van Schaik, Timo B.,Mouarrawis, Valentinos,de Wit, Martin J. M.,Velde, Christophe M. L. Vande,Ruijter, Eelco,Orru, Romano V. A.. "Efficient Diastereoselective Three-Component Synthesis of Pipecolic Amides". . p. 5313 - 5325. Retrieved 2019/06/10.