4-((1S,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(dimethylamino)ethylcarbamoyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-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

Base Information

• Chemical Name: 4-((1S,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(dimethylamino)ethylcarbamoyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-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
• CAS No.: 1351278-20-0
• Molecular Formula: C₄₁H₆₂N₂O₃
• Molecular Weight: 630.955

Synonyms:4-((1S,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(dimethylamino)ethylcarbamoyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-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

Chemical Property of 4-((1S,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(dimethylamino)ethylcarbamoyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-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

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Technology Process of 4-((1S,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(dimethylamino)ethylcarbamoyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-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

There total 11 articles about 4-((1S,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(dimethylamino)ethylcarbamoyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-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 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: 36.0%

methyl 4-((1S,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(dimethylamino)ethylcarbamoyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-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 (1351278-96-0) → 4-((1S,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(dimethylamino)ethylcarbamoyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-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 (1351278-20-0)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; at 78 ℃; for 3h;

Reference yield:

Betulinic acid (472-15-1) → 4-((1S,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(dimethylamino)ethylcarbamoyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-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 (1351278-20-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: hydrogen; methanol / palladium 10% on activated carbon / ethyl acetate; methanol / 18 h / 20 °C / 2327.23 Torr

2.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 60 °C

3.1: pyridinium chlorochromate / dichloromethane / 4 h

4.1: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / -78 °C

4.2: 2.33 h / -78 °C

5.1: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 2 h / 90 °C / Inert atmosphere

6.1: triethylamine / palladium diacetate / dichloromethane / 3 h / 60 °C / Inert atmosphere

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

8.1: thionyl chloride / dichloromethane / 2 h / 20 °C

9.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C

10.1: sodium hydroxide / 1,4-dioxane / 3 h / 78 °C

With methanol; thionyl chloride; tetrabutyl ammonium fluoride; hydrogen; potassium hexamethylsilazane; sodium carbonate; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium 10% on activated carbon; palladium diacetate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

Reference yield:

dihydrobetulinic acid (38736-78-6,25488-53-3) → 4-((1S,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(dimethylamino)ethylcarbamoyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-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 (1351278-20-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 60 °C

2.1: pyridinium chlorochromate / dichloromethane / 4 h

3.1: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / -78 °C

3.2: 2.33 h / -78 °C

4.1: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 2 h / 90 °C / Inert atmosphere

5.1: triethylamine / palladium diacetate / dichloromethane / 3 h / 60 °C / Inert atmosphere

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

7.1: thionyl chloride / dichloromethane / 2 h / 20 °C

8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C

9.1: sodium hydroxide / 1,4-dioxane / 3 h / 78 °C

With thionyl chloride; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; sodium carbonate; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium diacetate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;

upstream raw materials:

Betulinic acid

dihydrobetulinic acid

methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(dimethylamino)ethylcarbamoyl)-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-((1S,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(dimethylamino)ethylcarbamoyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-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

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