1,2-Pyrrolidinedicarboxylic acid, 4-[(3-chloro-7-Methoxy-2-quinoxalinyl)oxy]-, 1-(1,1-diMethylethyl) 2-Methyl ester,(2S,4R)-

Base Information

• Chemical Name: 1,2-Pyrrolidinedicarboxylic acid, 4-[(3-chloro-7-Methoxy-2-quinoxalinyl)oxy]-, 1-(1,1-diMethylethyl) 2-Methyl ester,(2S,4R)-
• CAS No.: 1206524-79-9
• Molecular Formula: C20H24ClN3O6
• Molecular Weight: 437.88
• Mol file: 1206524-79-9.mol

Synonyms:1,2-Pyrrolidinedicarboxylic acid, 4-[(3-chloro-7-Methoxy-2-quinoxalinyl)oxy]-, 1-(1,1-diMethylethyl) 2-Methyl ester,(2S,4R)-;(2S,4R)-1-tert-butyl 2-Methyl 4-((3-chloro-7-Methoxyquinoxalin-2-yl)oxy)pyrrolidine-1,2-dicarboxylate;Grazoprevir Intermediate 2

Chemical Property of 1,2-Pyrrolidinedicarboxylic acid, 4-[(3-chloro-7-Methoxy-2-quinoxalinyl)oxy]-, 1-(1,1-diMethylethyl) 2-Methyl ester,(2S,4R)-

Chemical Property:

• Boiling Point: 524.2±50.0 °C(Predicted)
• PKA: -1.42±0.48(Predicted)
• PSA: 100.08000
• Density: 1.324±0.06 g/cm3(Predicted)
• LogP: 3.15950

Purity/Quality:

98% ^*data from raw suppliers

1,2-Pyrrolidinedicarboxylicacid,4-[(3-chloro-7-methoxy-2-quinoxalinyl)oxy]-,1-(1,1-dimethylethyl)2-methylester,(2S,4R)- ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2S,4R)-4-[(3-Chloro-7-methoxy-2-quinoxalinyl)oxy]-,1-(1,1-dimethylethyl),- 1,2-Pyrrolidinedicarboxylic Acid 2-Methyl Ester acts as a reagent in the discovery of MK-5172 (M424985), a macrocyclic analog as an antiviral protease inhibitor. Reagent in the discovery of quinoxaline-based metathesis catalysts from the synthesis of Grazoprevir. It is a COVID19-related research product.

Technology Process of 1,2-Pyrrolidinedicarboxylic acid, 4-[(3-chloro-7-Methoxy-2-quinoxalinyl)oxy]-, 1-(1,1-diMethylethyl) 2-Methyl ester,(2S,4R)-

There total 14 articles about 1,2-Pyrrolidinedicarboxylic acid, 4-[(3-chloro-7-Methoxy-2-quinoxalinyl)oxy]-, 1-(1,1-diMethylethyl) 2-Methyl ester,(2S,4R)- 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: 88.0%

2,3-dichloro-6-methoxyquinoxaline (39267-04-4) + 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate (74844-91-0) → 1-(tert-butyl) 2-methyl (2S,4R)-4-((3-chloro-7-methoxyquinoxalin-2-yl)oxy)pyrrolidine-1,2-dicarboxylate (1206524-79-9)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl acetamide; at 40 - 45 ℃; for 35h;

DOI:10.1021/acs.orglett.8b03173

Reference yield: 76.0%

3-chloro-7-methoxyquinoxalin-2(1H)-one (1263814-66-9) + 1-tert-butyl 2-methyl (2S,4S)-4-{[(4-bromo-phenyl)sulfonyl]oxy}-pyrrolidine-1,2-dicarboxylate (438452-29-0) → 1-(tert-butyl) 2-methyl (2S,4R)-4-((3-chloro-7-methoxyquinoxalin-2-yl)oxy)pyrrolidine-1,2-dicarboxylate (1206524-79-9)

Guidance literature:

3-chloro-7-methoxyquinoxalin-2(1H)-one; With 1-methyl-pyrrolidin-2-one; caesium carbonate; at 20 ℃; for 0.25h; Inert atmosphere;

1-tert-butyl 2-methyl (2S,4S)-4-{[(4-bromo-phenyl)sulfonyl]oxy}-pyrrolidine-1,2-dicarboxylate; at 55 ℃; Inert atmosphere;

DOI:10.1021/acs.jmedchem.7b00426

Reference yield: 76.0%

→ 1-(tert-butyl) 2-methyl (2S,4R)-4-((3-chloro-7-methoxyquinoxalin-2-yl)oxy)pyrrolidine-1,2-dicarboxylate (1206524-79-9)

Guidance literature:

With caesium carbonate; In 1-methyl-pyrrolidin-2-one; at 20 ℃; for 0.25h; Inert atmosphere;

In 1-methyl-pyrrolidin-2-one; at 55 ℃; for 6h; Inert atmosphere;

upstream raw materials:

3-chloro-6-methoxyquinoxalin-2-ol

1-tert-butyl 2-methyl (2S,4S)-4-{[(4-bromo-phenyl)sulfonyl]oxy}-pyrrolidine-1,2-dicarboxylate

2,3-dihydroxy-6-methoxyquinoxaline

4-methoxyphenylene-1,2-diamine dihydrochloride

Downstream raw materials:

methyl (4R)-4-[(3-chloro-7-methoxyquinoxalin-2-yl)oxy]-L-prolinate hydrochloride

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

(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

Refernces

• 1、 Harper, Steven,McCauley, John A.,Rudd, Michael T.,Ferrara, Marco,DiFilippo, Marcello,Crescenzi, Benedetta,Koch, Uwe,Petrocchi, Alessia,Holloway, M. Katharine,Butcher, John W.,Romano, Joseph J.,Bush, Kimberly J.,Gilbert, Kevin F.,McIntyre, Charles J.,Nguyen, Kevin T.,Nizi, Emanuela,Carroll, Steven S.,Ludmerer, Steven W.,Burlein, Christine,Dimuzio, Jillian M.,Graham, Donald J.,McHale, Carolyn M.,Stahlhut, Mark W.,Olsen, David B.,Monteagudo, Edith,Cianetti, Simona,Giuliano, Claudio,Pucci, Vincenzo,Trainor, Nicole,Fandozzi, Christine M.,Rowley, Michael,Coleman, Paul J.,Vacca, Joseph P.,Summa, Vincenzo,Liverton, Nigel J.. "Discovery of MK-5172, a macrocyclic hepatitis C virus NS3/4a protease inhibitor". . p. 332 - 336. Retrieved 2012.
• 2、 -. "HEPATITIS C VIRUS NS3/4A PROTEASE INHIBITORS". Paragraph 00196; 00197; 00303. . Retrieved 2019/01/11.