Nelfinavir mesylate

Base Information

• Chemical Name: Nelfinavir mesylate
• CAS No.: 159989-65-8
• Molecular Formula: C32H45N3O4S^.CH4O3S
• Molecular Weight: 663.9
• Hs Code.: 29334900
• Mol file: 159989-65-8.mol

Synonyms:Nelfinavir nesylate;[(3S-(3R*,4aR*,8aR*,2S*,3S*)]-2-[2-Hydroxy-3-phenylthiomethyl-4-aza-5-oxo-5-(2-methyl-3-hydroxy-phenyl)pentyl]-decahydroisoquinoline-3-N-t-butylcarboxamide methanesulfonic acid);3-Isoquinolinecarboxamide, N-(1,1-dimethylethyl)decahydro-2-((2R,3R)-2-hydroxy-3-((3-hydroxy-2-methylbenzoyl)amino)-4-(phenylthio)butyl)-, (3S,4aS,8aS)-;Nelfinavir mesylate (USAN);3-Isoquinolinecarboxamide, N-(1,1-dimethylethyl)decahydro-2-((2R,3R)-2-hydroxy-3-((3-hydroxy-2-methylbenzoyl)amino)-4-(phenylthio)butyl)-, (3S,4aS,8aS)-, monomethanesulfonate (salt);Nelfinavir mesilate (JAN);(3S,4aS,8aS)-2-[(2R,3R)-2-hydroxy-3-[(3-hydroxy-2-methyl-benzoyl)amino]-4-phenylsulfanyl-butyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide;NLF;AG1343 (*Mesylate salt*);(3S-(2(2S*,3S*),3alpha,4abeta,8abeta))-N-(1,1-Dimethylethyl)decahydro-2-(2-hydroxy-3-((3-hydroxy-2-methylbenzoyl)amino)-4-(phenylthio)butyl)-3-isoquinolinecarboxamide;AG 1343;Nelfinavir [INN:BAN];3-Isoquinolinecarboxamide, N-(1,1-dimethylethyl)decahydro-2-(2-hydroxy-3-((3-hydroxy-2-methylbenzoyl)amino)-4-(phenylthio)butyl)-, (3S-(2-(2S*,3S*),3-alpha,4a-beta,8a-beta))-;3-Isoquinolinecarboxamide, N-(1,1-dimethylethyl)decahydro-2-(2-hydroxy-3-((3-hydroxy-2-methylbenzoyl)amino)-4-(phenylthio)butyl)-, (3S-(2(2,S*,3S*),3-alpha,4a-beta,8a-beta))-, monomethanesulfonate (salt);Viracept (TN);N-(1,1-Dimethylethyl)decahydro-2-(2-hydroxy-3-((3-hydroxy-2-methylbenzoyl)amino)-4-(phenylthio)butyl)-3-isoquinolinecarboxamide (3S-(2(2S*,3S*),3alpha,4abeta,8abeta))-;(3S,4aS,8aS)-N-(1,1-Dimethylethyl)decahydro-2-[(2R,3R)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-(phenylthio)butyl]-3-isoquinolinecarboxamide mesylate;

Chemical Property of Nelfinavir mesylate

Chemical Property:

• Appearance/Colour: white powder
• Melting Point: 131-135 °C
• Boiling Point: 786.8 °C at 760 mmHg
• PKA: pKa -1.20(at 25℃)
• Flash Point: 429.7 °C
• PSA: 189.95000
• LogP: 6.05210
• Storage Temp.: Store at +4°C
• Solubility.: DMSO: ≥2mg/mL
• Water Solubility.: 4.5g/L(temperature not stated)
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 10
• Exact Mass: 663.30119326
• Heavy Atom Count: 45
• Complexity: 909

Purity/Quality:

98% ^*data from raw suppliers

Nelfinavir, Mesylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C(C=CC=C1O)C(=O)NC(CSC2=CC=CC=C2)C(C[NH+]3CC4CCCCC4CC3C(=O)NC(C)(C)C)O.CS(=O)(=O)[O-]
• Isomeric SMILES: CC1=C(C=CC=C1O)C(=O)N[C@@H](CSC2=CC=CC=C2)[C@@H](C[NH+]3C[C@H]4CCCC[C@H]4C[C@H]3C(=O)NC(C)(C)C)O.CS(=O)(=O)[O-]
• Description: Viracept was launched in the US as an orally-available, non-peptidic HIV protease inhibitor. It is prepared in an eight step synthesis beginning with N- (benzyloxycarbonyl)-L-serine β-lactone. The HIV protease inhibitory activity blocks the processing of gag and gagpol polyproteins that are required for viral maturation. It was discovered based on an experimentally derived 3D-structure of HIV-1 protease. Viracept has a high oral bioavailability, lacks toxicity, and has a resistance profile different from other protease inhibitors. Viracept with ziduvudine and larnivudine generated a 98% mean reduction from baseline in viral load after 24 weeks compared to ziduvudine and larnivudine alone. Viracept also had better CD4 counts and is available in adult and pediatric formulations.
• Uses: Nelfinavir Mesylate is an antiviral. HIV protease inhibitor. It is a COVID19-related research product. An antiviral. HIV protease inhibitor.

Technology Process of Nelfinavir mesylate

There total 5 articles about Nelfinavir mesylate 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: 98.0%

methanesulfonic acid (75-75-2,98527-29-8) + nelfinavir (159989-64-7) → nelfinavir mesylate (159989-65-8)

Guidance literature:

In acetone; at 20 - 35 ℃; for 2h; Product distribution / selectivity;

Reference yield: 95.0%

methyltertbutyl ether (67000-01-5) + nelfinavir (159989-64-7) → nelfinavir mesylate (159989-65-8)

Guidance literature:

With methanesulfonic acid; In tetrahydrofuran;

Reference yield: 93.0%

→ nelfinavir mesylate (159989-65-8)

Guidance literature:

In methanol; at 25 - 30 ℃; for 0.25h; Carbon;

at 45 - 55 ℃; for 1h; under 10 - 200 Torr;

In tert-butyl methyl ether; at 25 - 30 ℃; for 0.25h; Purification / work up;

upstream raw materials:

methanesulfonic acid

nelfinavir

methyltertbutyl ether

(2R,3R)-4-((3S,4aS,8aS)-3-(tertbutylcarbamoyl)octahydroisoquinolin-2(1H)-yl)-3-hydroxy-1-(phenylthio)butan-2-aminium benzoate

Refernces

• 1、 -. "AN IMPROVED PROCESS FOR PREPARATION OF AMORPHOUS NELFINAVIR MESYLATE". Page/Page column 8. . Retrieved 2008/06/13.
• 2、 -. "Method of making a HIV-Protease inhibitor". Page/Page column 30. . Retrieved 2010/11/30.