(3beta)-3-(3-Carboxy-3-methyl-1-oxobutoxy)-N-[1-(4-chlorophenyl)cyclopropyl]-alpha,21-dioxo-28-norlup-18-ene-17-acetamide

Base Information

• Chemical Name: (3beta)-3-(3-Carboxy-3-methyl-1-oxobutoxy)-N-[1-(4-chlorophenyl)cyclopropyl]-alpha,21-dioxo-28-norlup-18-ene-17-acetamide
• CAS No.: 1422355-59-6
• Molecular Formula: C46H62ClNO7
• Molecular Weight: 776.454
• Mol file: 1422355-59-6.mol

Synonyms:(3beta)-3-(3-Carboxy-3-methyl-1-oxobutoxy)-N-[1-(4-chlorophenyl)cyclopropyl]-alpha,21-dioxo-28-norlup-18-ene-17-acetamide;GSK2578999

Chemical Property of (3beta)-3-(3-Carboxy-3-methyl-1-oxobutoxy)-N-[1-(4-chlorophenyl)cyclopropyl]-alpha,21-dioxo-28-norlup-18-ene-17-acetamide

Chemical Property:

• PSA: 126.84000
• LogP: 9.79870

Purity/Quality:

99%+, ^*data from raw suppliers

GSK2578999A ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3beta)-3-(3-Carboxy-3-methyl-1-oxobutoxy)-N-[1-(4-chlorophenyl)cyclopropyl]-alpha,21-dioxo-28-norlup-18-ene-17-acetamide

There total 22 articles about (3beta)-3-(3-Carboxy-3-methyl-1-oxobutoxy)-N-[1-(4-chlorophenyl)cyclopropyl]-alpha,21-dioxo-28-norlup-18-ene-17-acetamide 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: 82.0%

C50H70ClNO7 (1422356-30-6) → 4-((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-(2-(1-(4-chlorophenyl)-cyclopropylamino)-2-oxoacetyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-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 (1422355-59-6)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;

Reference yield:

(3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-formyl-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-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 (1326311-90-3) → 4-((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-(2-(1-(4-chlorophenyl)-cyclopropylamino)-2-oxoacetyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-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 (1422355-59-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -40 - -20 °C / Inert atmosphere

1.2: 1 h / -78 - -70 °C / Inert atmosphere

2.1: triethylamine; dmap / dichloromethane / 2 h / 20 - 50 °C

3.1: N-Bromosuccinimide / acetonitrile; water / 0.17 h / 20 °C

4.1: 2-methyl-but-2-ene; sodium chlorite; sodium dihydrogenphosphate / tetrahydrofuran; water; tert-butyl alcohol / 0.92 h / 0 - 20 °C

5.1: potassium hydroxide / toluene; ethanol / 0.5 h / 20 °C

6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 3 h / 50 °C

7.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 1 h / 0 - 20 °C

8.1: hydrogenchloride; water / 20 - 45 °C

9.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 1 h / 20 °C

10.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

With hydrogenchloride; dmap; sodium chlorite; sodium dihydrogenphosphate; N-Bromosuccinimide; n-butyllithium; 2-methyl-but-2-ene; water; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; potassium hydroxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;

Reference yield:

betulin diacetate (1721-69-3) → 4-((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-(2-(1-(4-chlorophenyl)-cyclopropylamino)-2-oxoacetyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-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 (1422355-59-6)

Guidance literature:

Multi-step reaction with 11 steps

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

2: acetic acid; sodium acetate; sodium dichromate dihydrate; acetic anhydride / toluene / 60 °C

3: potassium hydroxide / toluene; ethanol / 1 h / 20 °C

4: pyridinium chlorochromate / dichloromethane / 1 h / 20 °C

5: triethylamine / 20 °C

6: Dess-Martin periodane / dichloromethane / 2 h / 20 °C

7: acetic acid; sodium nitrite / dimethyl sulfoxide / 0 - 20 °C

8: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 1 h / 0 - 20 °C

9: hydrogenchloride; water / 20 - 45 °C

10: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 1 h / 20 °C

11: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

With hydrogenchloride; dmap; sodium dichromate dihydrate; water; hydrogen bromide; sodium acetate; acetic anhydride; Dess-Martin periodane; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; pyridinium chlorochromate; trifluoroacetic acid; potassium hydroxide; sodium nitrite; In ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

upstream raw materials:

((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-acetoxy-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-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

(3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-(hydroxymethyl)-1-isopropyl-5a,5b,8, 8,11a-pentamethyl-2-oxo-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

(3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-formyl-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-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

(3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((1,3-dithian-2-yl)(hydroxy)methyl)-9-hydroxy-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-2-one

Downstream raw materials:

{[(4-{[(1R,2R,5R,10S,13R,14R,17S,19R)-5-({[1-(4-chlorophenyl)cyclopropyl]carbamoyl}(oxo)methyl)-1,2,14,18,18-pentamethyl-7-oxo-8-(propan-2-yl)pentacyclo[11.8.0.0^2,10.0^5,9.0^14,19]henicos-8-en-17-yl]oxy}-2,2-dimethyl-4-oxobutanoyl)oxy]methoxy}phosphonic acid

{2-[(4-{[(1R,2R,10S,13S,14R,17S,19R)-5-({[1-(4-chlorophenyl)cyclopropyl]carbamoyl}(oxo)methyl)-1,2,14,18,18-pentamethyl-7-oxo-8-(propan-2-yl)pentacyclo[11.8.0.0^2,10.0^5,9.0^14,19]henicos-8-en-17-yl]oxy}-2,2-dimethyl-4-oxobutanoyl)oxy]ethoxy}phosphonic acid

C₅₆H₈₃ClNO₁₁P

(1R,2R,5R,10S,13R,14R,17S,19R)-5-({[1-(4-chlorophenyl)cyclopropyl]carbamoyl}(oxo)methyl)-1,2,14,18,18-pentamethyl-7-oxo-8-(propan-2-yl)pentacyclo[11,8.0.0^2,10.0^5,9.0^14,19]henicos-8-en-17-yl 1-(2-hydroxyethyl)2,2-dimethylbutanedioate

Refernces

• 1、 -. "CARBONYL DERIVATIVES OF BETULIN". . . Retrieved 2013/03/26.