methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(chlorocarbonyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate

Base Information

• Chemical Name: methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(chlorocarbonyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate
• CAS No.: 1351278-78-8
• Molecular Formula: C₃₈H₅₁ClO₃
• Molecular Weight: 591.274
• Mol file: 1351278-78-8.mol

Synonyms:methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(chlorocarbonyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate

Chemical Property of methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(chlorocarbonyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(chlorocarbonyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate

There total 7 articles about methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(chlorocarbonyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate 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: 99.0%

(1R,3aS,5aR,5bR,7aR,11aS,11bR,13 aR,13bR)-9-(4-(methoxycarbonyl)phenyl)-5 a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid (1350914-72-5) → methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(chlorocarbonyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate (1351278-78-8)

Guidance literature:

With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃;

Reference yield:

Betulinic acid (472-15-1) → methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(chlorocarbonyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate (1351278-78-8)

Guidance literature:

Multi-step reaction with 7 steps

1: potassium carbonate / N,N-dimethyl-formamide / 3.5 h / 60 °C

2: pyridinium chlorochromate / dichloromethane / 5.5 h

3: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C

4: sodium carbonate monohydrate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / isopropyl alcohol; 1,4-dioxane; water / Inert atmosphere; Reflux

5: triethylamine / palladium diacetate / 1,2-dichloro-ethane / 2 h / 60 °C / Inert atmosphere

6: tetrabutyl ammonium fluoride / 1,4-dioxane; water / 4 h / 20 °C

7: thionyl chloride / dichloromethane / 20 °C

With thionyl chloride; sodium carbonate monohydrate; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; potassium carbonate; triethylamine; pyridinium chlorochromate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium diacetate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; isopropyl alcohol;

Reference yield:

(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR 13bR)-benzyl 9-(4-(methoxycarbonyl)phenyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysene-3a-carboxylate (1350915-22-8) → methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(chlorocarbonyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate (1351278-78-8)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / palladium diacetate / 1,2-dichloro-ethane / 2 h / 60 °C / Inert atmosphere

2: tetrabutyl ammonium fluoride / 1,4-dioxane; water / 4 h / 20 °C

3: thionyl chloride / dichloromethane / 20 °C

With thionyl chloride; tetrabutyl ammonium fluoride; triethylamine; palladium diacetate; In 1,4-dioxane; dichloromethane; water; 1,2-dichloro-ethane;

upstream raw materials:

Betulinic acid

benzyl (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylate

(1R,3aS,5aR,5bR,7aR,11aS,11bR,13 aR,13bR)-9-(4-(methoxycarbonyl)phenyl)-5 a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid

benzyl (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-oxo-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylate

Downstream raw materials:

4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-3a-((2-(pyridin-2-yl)ethyl)carbamoyl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoic acid

methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-((tert-butoxycarbonyl)(methyl)amino)ethyl)carbamoyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate

methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-((2-methoxy-2-oxoethyl)amino)ethyl)carbamoyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate

Refernces

• 1、 Swidorski, Jacob J.,Liu, Zheng,Sit, Sing-Yuen,Chen, Jie,Chen, Yan,Sin, Ny,Venables, Brian L.,Parker, Dawn D.,Nowicka-Sans, Beata,Terry, Brian J.,Protack, Tricia,Rahematpura, Sandhya,Hanumegowda, Umesh,Jenkins, Susan,Krystal, Mark,Dicker, Ira B.,Meanwell, Nicholas A.,Regueiro-Ren, Alicia. "Inhibitors of HIV-1 maturation: Development of structure-activity relationship for C-28 amides based on C-3 benzoic acid-modified triterpenoids". supporting information. p. 1925 - 1930. Retrieved 2016/04/09.