4-((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-(2-(4-chlorobenzylamino)acetyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yloxy)-2,2-dimethyl-4-oxobutanoic acid

Base Information

• Chemical Name: 4-((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-(2-(4-chlorobenzylamino)acetyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yloxy)-2,2-dimethyl-4-oxobutanoic acid
• CAS No.: 1326312-26-8
• Molecular Formula: C₄₄H₆₄ClNO₅
• Molecular Weight: 722.449
• Mol file: 1326312-26-8.mol

Synonyms:4-((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-(2-(4-chlorobenzylamino)acetyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yloxy)-2,2-dimethyl-4-oxobutanoic acid

Chemical Property of 4-((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-(2-(4-chlorobenzylamino)acetyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yloxy)-2,2-dimethyl-4-oxobutanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-(2-(4-chlorobenzylamino)acetyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yloxy)-2,2-dimethyl-4-oxobutanoic acid

There total 12 articles about 4-((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-(2-(4-chlorobenzylamino)acetyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yloxy)-2,2-dimethyl-4-oxobutanoic 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: 77.0%

4-{[(1R,2R,5S,10S,13R,14R,17S,19R)-5-(2-{[(tert-butoxy)carbonyl][(4-chlorophenyl)methyl]amino}acetyl)-1,2,14,18,18-pentamethyl-8-(propan-2-yl)pentacyclo[11.8.0.02,10.05,9.014,19]henicos-8-en-17-yl]oxy}-2,2-dimethyl-4-oxobutanoic acid (1326312-25-7) → 4-((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-(2-(4-chlorobenzylamino)acetyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yloxy)-2,2-dimethyl-4-oxobutanoic acid (1326312-26-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;

Reference yield:

(3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-(2-amino-1-hydroxyethyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yl acetate (1326312-20-2) → 4-((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-(2-(4-chlorobenzylamino)acetyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yloxy)-2,2-dimethyl-4-oxobutanoic acid (1326312-26-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: zinc(II) chloride / dichloromethane; methanol / 1 h / 80 °C

1.2: 1 h / 20 °C

2.1: triethylamine / 0.5 h / 20 °C

3.1: silica gel; pyridinium chlorochromate / dichloromethane / 2 h / 20 °C

4.1: sodium hydroxide; water / tetrahydrofuran; methanol / 1 h / 20 °C

5.1: dmap; pyridine / 80 °C

6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

With pyridine; dmap; water; silica gel; triethylamine; pyridinium chlorochromate; trifluoroacetic acid; sodium hydroxide; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane;

Reference yield:

betulin (473-98-3) → 4-((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-(2-(4-chlorobenzylamino)acetyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yloxy)-2,2-dimethyl-4-oxobutanoic acid (1326312-26-8)

Guidance literature:

Multi-step reaction with 12 steps

1.1: dmap; triethylamine / dichloromethane / Reflux

2.1: acetic anhydride; hydrogen bromide; acetic acid / toluene / 1.5 h / 105 °C

3.1: potassium hydroxide / toluene; ethanol / 4 h / 20 °C

4.1: silica gel; pyridinium chlorochromate / dichloromethane / 2 h / 20 °C

5.1: triethylamine / dichloromethane / 60 °C

6.1: sodium tetrahydroborate; nickel dichloride; methanol / 0.17 h / 0 °C

7.1: zinc(II) chloride / dichloromethane; methanol / 1 h / 80 °C

7.2: 1 h / 20 °C

8.1: triethylamine / 0.5 h / 20 °C

9.1: silica gel; pyridinium chlorochromate / dichloromethane / 2 h / 20 °C

10.1: sodium hydroxide; water / tetrahydrofuran; methanol / 1 h / 20 °C

11.1: dmap; pyridine / 80 °C

12.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

With pyridine; methanol; dmap; sodium tetrahydroborate; water; hydrogen bromide; acetic anhydride; silica gel; acetic acid; triethylamine; pyridinium chlorochromate; trifluoroacetic acid; potassium hydroxide; sodium hydroxide; nickel dichloride; zinc(II) chloride; In tetrahydrofuran; methanol; ethanol; dichloromethane; toluene;

upstream raw materials:

betulin diacetate

betulin

((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-acetoxy-1-isopropyl-5a,5b,8,8,11a-pentamethyl-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-3a-yl)methyl acetate

2,2-dimethylsuccinic anhydride

Refernces

• 1、 -. "DERIVATIVES OF BETULIN". . . Retrieved 2011/09/15.