MK-5172

Base Information

• Chemical Name: MK-5172
• CAS No.: 1206524-85-7
• Molecular Formula: C29H38N4O7
• Molecular Weight: 554.643
• Mol file: 1206524-85-7.mol

Synonyms:(1aR,5S,8S,10R,22aR)-5-(1,1-Dimethylethyl)-1,1a,3,4,5,6,9,10,18,19,20,21,22,22a-tetradecahydro-14-methoxy-3,6-dioxo-8H-7,10-methanocyclopropa[18,19][1,10,3,6]dioxadiazacyclononadecino[11,12-b]quinoxaline-8-carboxylic acid;

Chemical Property of MK-5172

Chemical Property:

• Boiling Point: 824.997 °C at 760 mmHg
• PKA: 3.23±0.40(Predicted)
• Flash Point: 452.742 °C
• PSA: 143.67000
• Density: 1.331 g/cm³
• LogP: 3.29510
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility.: Acetone (Slightly), Chloroform (Slightly), DMSO (Slightly, Sonicated), Methanol

Purity/Quality:

98% ^*data from raw suppliers

MK 5172 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: MK-?5172 is a selective inhibitor of hepatitis C virus NS3?/4a protease with broad activity across genotypes and resistant variants.

Technology Process of MK-5172

There total 34 articles about MK-5172 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: 100.0%

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 (1206524-84-6) → (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:

With lithium hydroxide monohydrate; water; In tetrahydrofuran; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1021/ml300017p

Reference yield:

C30H40N4O7 → (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:

With sodium hydroxide; In methanol; at 20 - 50 ℃;

Reference yield:

1-(tert-butyl) 2-methyl (2S,4R)-4-((3-chloro-7-methoxyquinoxalin-2-yl)oxy)pyrrolidine-1,2-dicarboxylate (1206524-79-9) → (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 6 steps

1: hydrogenchloride / 1,4-dioxane / 2 h / Inert atmosphere

2: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; triethylamine / ethanol / 1 h / Inert atmosphere; Reflux

4: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / 1,2-dichloro-ethane / 1 h / 90 °C / Inert atmosphere

5: palladium 10% on activated carbon; hydrogen / 1,4-dioxane; methanol / 2 h

6: lithium hydroxide monohydrate; water / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere

With hydrogenchloride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; lithium hydroxide monohydrate; 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride; palladium 10% on activated carbon; water; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/ml300017p

upstream raw materials:

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

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

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

trans 2-(pent-4-en-1-yl)cyclopropanol

Downstream raw materials:

grazoprevir

Refernces

• 1、 -. "METHODS AND INTERMEDIATES FOR PREPARING MACROLACTAMS". Page/Page column 44-45. . Retrieved 2015/05/05.
• 2、 Kuethe, Jeffrey,Zhong, Yong-Li,Yasuda, Nobuyoshi,Beutner, Gregory,Linn, Katherine,Kim, Mary,Marcune, Benjamin,Dreher, Spencer Douglas,Humphrey, Guy,Pei, Tao. "Development of a practical, asymmetric synthesis of the hepatitis C virus protease inhibitor MK-5172". supporting information. p. 4174 - 4177. Retrieved 2013/09/12.