methyl (2S,4R)-4-((3-chloro-7-methoxyquinoxalin-2-yl)oxy)-2-(methoxycarbonyl)pyrrolidinium methanesulfonate

Base Information

• Chemical Name: methyl (2S,4R)-4-((3-chloro-7-methoxyquinoxalin-2-yl)oxy)-2-(methoxycarbonyl)pyrrolidinium methanesulfonate
• CAS No.: 1425038-20-5
• Molecular Formula: CH₄O₃S*C₁₅H₁₆ClN₃O₄
• Molecular Weight: 433.87
• Mol file: 1425038-20-5.mol

Synonyms:(2S,4R)-4-[(3-chloro-7-methoxyquinoxalin-2-yl)oxy]-2-(methoxycarbonyl)pyrrolidin-1-ium methanesulfonate

Chemical Property of methyl (2S,4R)-4-((3-chloro-7-methoxyquinoxalin-2-yl)oxy)-2-(methoxycarbonyl)pyrrolidinium methanesulfonate

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

(2S,4R)-4-((3-Chloro-7-methoxyquinoxalin-2-yl)oxy)-2-(methoxycarbonyl)pyrrolidiniumMethanesulfonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2S,4R)-4-((3-Chloro-7-methoxyquinoxalin-2-yl)oxy)-2-(methoxycarbonyl)pyrrolidinium Methanesulfonate is an antiviral agent and Grazoprevir (M424985) intermediate. Grazoprevir is a second-generation NS3/4A protease inhibitor. It is a COVID19-related research product.

Technology Process of methyl (2S,4R)-4-((3-chloro-7-methoxyquinoxalin-2-yl)oxy)-2-(methoxycarbonyl)pyrrolidinium methanesulfonate

There total 1 articles about methyl (2S,4R)-4-((3-chloro-7-methoxyquinoxalin-2-yl)oxy)-2-(methoxycarbonyl)pyrrolidinium methanesulfonate 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: 94.5%

methanesulfonic acid (75-75-2,98527-29-8) + 2,3-dichloro-6-methoxyquinoxaline (39267-04-4) + L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → (2S,4R)-4-[(3-chloro-7-methoxyquinoxalin-2-yl)oxy]-2-(methoxycarbonyl)pyrrolidin-1-ium methanesulfonate (1425038-20-5)

Guidance literature:

2,3-dichloro-6-methoxyquinoxaline; L-4-hydroxyproline methyl ester hydrochloride; With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 23 - 30 ℃; for 15h;

methanesulfonic acid; at 20 - 30 ℃; for 10h; Temperature;

Reference yield:

(2S,4R)-4-[(3-chloro-7-methoxyquinoxalin-2-yl)oxy]-2-(methoxycarbonyl)pyrrolidin-1-ium methanesulfonate (1425038-20-5) → (1aR,5S,8S,10R,22aR)-5-tert-butyl-14-methoxy-3,6-dioxo-1,1a,3,4,5,6,9,10,18,19,20,21,22,22a-tetradeca-hydro-8H-7,10-methanocyclopropa[18,19][1,10,3,6]dioxadiazacyclononadecino[11,12-b]quinoxaline-8-carboxylic acid hydrate (1206524-85-7)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / methanol / 35 °C / Inert atmosphere

2: hydrogen; 10 wt% Pd(OH)2 on carbon / methanol / 5 h / 20 °C / 760.05 Torr

3: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl acetamide / 12 h / 0 °C / Inert atmosphere

4: sodium hydroxide / methanol / 50 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 10 wt% Pd(OH)2 on carbon; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; sodium hydroxide; In methanol; N,N-dimethyl acetamide;

Reference yield:

3-methyl-N-({[(1R,2R)-2-pent-4-en-1-ylcyclopropyl]oxy}carbonyl)-L-valine (1026200-27-0) + (2S,4R)-4-[(3-chloro-7-methoxyquinoxalin-2-yl)oxy]-2-(methoxycarbonyl)pyrrolidin-1-ium methanesulfonate (1425038-20-5) → (2S,4R)-methyl 4-((3-chloro-7-methoxyquinoxalin-2-yl)oxy)-1-((S)-3,3-dimethyl-2-((((1R,2R)-2-(pent-4-en-1-yl)cyclopropoxy)carbonyl)amino)butanoyl)pyrrolidine-2-carboxylate (1206524-81-3)

Guidance literature:

With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In acetonitrile; at 25 ℃;

upstream raw materials:

methanesulfonic acid

2,3-dichloro-6-methoxyquinoxaline

L-4-hydroxyproline methyl ester hydrochloride

Downstream raw materials:

methyl (1aR,5S,8S,10R,22aR)-5-tert-butyl-14-methoxy-3,6-dioxo-18,19-didehydro-1,1a,3,4,5,6,9,10,20,21,22,22a-dodecahydro-8H-7,10-methanocyclopropa[18,19][1,10,3, 6]dioxadiazacyclononadecino[11,12-b]quinoxaline-8-carboxylate

(1aR,5S,8S,10R,22aR)-5-tert-butyl-14-methoxy-3,6-dioxo-1,1a,3,4,5,6,9,10,18,19,20,21,22,22a-tetradeca-hydro-8H-7,10-methanocyclopropa[18,19][1,10,3,6]dioxadiazacyclononadecino[11,12-b]quinoxaline-8-carboxylic acid hydrate

grazoprevir

methyl (1aR,5S,8S,10R,22aR)-5-tert-butyl-14-methoxy-3,6-dioxo-1,1a,3,4,5,6,9,10,18,19,20,21,22,22a-tetradecahydro-8H-7,10-methanocyclopropa[18,19][1,10,3,6]dioxa-diazacyclononadecino[11,12-b]quinoxaline-8-carboxylate

Refernces