ethyl 2-(4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)acetate

Base Information

• Chemical Name: ethyl 2-(4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)acetate
• CAS No.: 1301198-39-9
• Molecular Formula: C₂₆H₃₂N₂O₅
• Molecular Weight: 452.55

Synonyms:ethyl 2-(4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)acetate

Chemical Property of ethyl 2-(4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2-(4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)acetate

There total 10 articles about ethyl 2-(4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)acetate 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: 59.7%

Ethyl 4-bromophenylacetate (14062-25-0) + 1-methylethyl [(2S,4R)-1-acetyl-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (1301198-32-2) → ethyl 2-(4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)acetate (1301198-39-9)

Guidance literature:

With potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 120 ℃; for 0.5h; Product distribution / selectivity; Inert atmosphere; Microwave irradiation;

Reference yield:

bromobenzene (108-86-1,52753-63-6) → ethyl 2-(4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)acetate (1301198-39-9)

Guidance literature:

Multi-step reaction with 8 steps

1: caesium carbonate / toluene / 0.75 h / Inert atmosphere

2: N-Bromosuccinimide / N,N-dimethyl-formamide / 0.33 h / Inert atmosphere; Cooling with ice bath

3: sulfuric acid / toluene / 2 h / 60 °C

4: lithium tert-butoxide / ethyl acetate; tetrahydrofuran / 0.5 h / -9 °C

5: sodium tetrahydroborate; magnesium(II) chloride hexahydrate / ethanol; water / 2 h / -10 - 20 °C

6: pyridine / dichloromethane / Inert atmosphere

7: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 6 h / 80 °C / Inert atmosphere

8: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 0.5 h / 120 °C / Microwave irradiation

With pyridine; sodium tetrahydroborate; N-Bromosuccinimide; magnesium(II) chloride hexahydrate; sulfuric acid; potassium acetate; potassium carbonate; caesium carbonate; lithium tert-butoxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene;

Reference yield:

(S)-3-(N-phenylamino)-butyronitrile (680188-22-1) → ethyl 2-(4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)acetate (1301198-39-9)

Guidance literature:

Multi-step reaction with 7 steps

1: N-Bromosuccinimide / N,N-dimethyl-formamide / 0.33 h / Inert atmosphere; Cooling with ice bath

2: sulfuric acid / toluene / 2 h / 60 °C

3: lithium tert-butoxide / ethyl acetate; tetrahydrofuran / 0.5 h / -9 °C

4: sodium tetrahydroborate; magnesium(II) chloride hexahydrate / ethanol; water / 2 h / -10 - 20 °C

5: pyridine / dichloromethane / Inert atmosphere

6: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 6 h / 80 °C / Inert atmosphere

7: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 0.5 h / 120 °C / Microwave irradiation

With pyridine; sodium tetrahydroborate; N-Bromosuccinimide; magnesium(II) chloride hexahydrate; sulfuric acid; potassium acetate; potassium carbonate; lithium tert-butoxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene;

upstream raw materials:

4-bromo-aniline

bromobenzene

Ethyl 4-bromophenylacetate

1-methylethyl [(2S,4R)-1-acetyl-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydro-4-quinolinyl]carbamate

Downstream raw materials:

2-(4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)acetic acid

1-methylethyl {(2S,4R)-1-acetyl-6-[4-(2-{[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]amino}-2-oxoethyl)phenyl]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate

isopropyl ((2S,4R)-1-acetyl-6-(4-(2-((2-aminoethyl)amino)-2-oxoethyl)phenyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)carbamate hydrochloride

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