7-benzyloxy-2-[(4-tert-butoxycarbonylamino)phenyl]-1,2-dihydro-1-oxo-4-(3,4,5-trimethoxyphenyl)-3-isoquinolinecarboxylic acid

Base Information

• Chemical Name: 7-benzyloxy-2-[(4-tert-butoxycarbonylamino)phenyl]-1,2-dihydro-1-oxo-4-(3,4,5-trimethoxyphenyl)-3-isoquinolinecarboxylic acid
• CAS No.: 347423-83-0
• Molecular Formula: C₃₇H₃₆N₂O₉
• Molecular Weight: 652.701

Synonyms:7-benzyloxy-2-[(4-tert-butoxycarbonylamino)phenyl]-1,2-dihydro-1-oxo-4-(3,4,5-trimethoxyphenyl)-3-isoquinolinecarboxylic acid

Chemical Property of 7-benzyloxy-2-[(4-tert-butoxycarbonylamino)phenyl]-1,2-dihydro-1-oxo-4-(3,4,5-trimethoxyphenyl)-3-isoquinolinecarboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-benzyloxy-2-[(4-tert-butoxycarbonylamino)phenyl]-1,2-dihydro-1-oxo-4-(3,4,5-trimethoxyphenyl)-3-isoquinolinecarboxylic acid

There total 8 articles about 7-benzyloxy-2-[(4-tert-butoxycarbonylamino)phenyl]-1,2-dihydro-1-oxo-4-(3,4,5-trimethoxyphenyl)-3-isoquinolinecarboxylic 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: 74.0%

N-(tert-butoxycarbonyl)-1,4-phenylenediamine (71026-66-9) + 7-benzyloxy-3,4-dihydro-3-hydroxy-4-(3,4,5-trimethoxyphenyl)-3-isocoumarincarboxylic acid (212501-44-5) → 7-benzyloxy-2-[(4-tert-butoxycarbonylamino)phenyl]-1,2-dihydro-1-oxo-4-(3,4,5-trimethoxyphenyl)-3-isoquinolinecarboxylic acid (347423-83-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In various solvent(s); at 110 ℃; for 8h;

DOI:10.1021/jm000558h

Reference yield:

N,N-dimethyl(3,4,5-trimethoxyphenyl)carboxamide (5658-49-1) → 7-benzyloxy-2-[(4-tert-butoxycarbonylamino)phenyl]-1,2-dihydro-1-oxo-4-(3,4,5-trimethoxyphenyl)-3-isoquinolinecarboxylic acid (347423-83-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: n-BuLi / tetrahydrofuran / 0.25 h / -78 °C

1.2: 81 percent / tetrahydrofuran / 0.5 h / -40 °C

2.1: 94 percent / 2 N HCl / tetrahydrofuran / 20 °C

3.1: 58 percent / resorcinol; acetate buffer; NaClO₂ / dioxane; H₂O / 20 °C / pH 3.8

4.1: K₂CO₃ / dimethylformamide / 20 °C

5.1: 4 N HCl / ethyl acetate / 20 °C

5.2: AcOH / dioxane / 6 h / Heating

6.1: 97 percent / 2 N aq. NaOH / tetrahydrofuran; methanol / 2 h / 20 °C

7.1: 74 percent / i-Pr₂NEt / various solvent(s) / 8 h / 110 °C

With hydrogenchloride; sodium hydroxide; sodium chlorite; n-butyllithium; acetate buffer; potassium carbonate; N-ethyl-N,N-diisopropylamine; recorcinol; In tetrahydrofuran; 1,4-dioxane; methanol; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm000558h

Reference yield:

5-(benzyloxy)-2-bromobenzaldehyde dimethylacetal (81418-49-7) → 7-benzyloxy-2-[(4-tert-butoxycarbonylamino)phenyl]-1,2-dihydro-1-oxo-4-(3,4,5-trimethoxyphenyl)-3-isoquinolinecarboxylic acid (347423-83-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: n-BuLi / tetrahydrofuran / 0.25 h / -78 °C

1.2: 81 percent / tetrahydrofuran / 0.5 h / -40 °C

2.1: 94 percent / 2 N HCl / tetrahydrofuran / 20 °C

3.1: 58 percent / resorcinol; acetate buffer; NaClO₂ / dioxane; H₂O / 20 °C / pH 3.8

4.1: K₂CO₃ / dimethylformamide / 20 °C

5.1: 4 N HCl / ethyl acetate / 20 °C

5.2: AcOH / dioxane / 6 h / Heating

6.1: 97 percent / 2 N aq. NaOH / tetrahydrofuran; methanol / 2 h / 20 °C

7.1: 74 percent / i-Pr₂NEt / various solvent(s) / 8 h / 110 °C

With hydrogenchloride; sodium hydroxide; sodium chlorite; n-butyllithium; acetate buffer; potassium carbonate; N-ethyl-N,N-diisopropylamine; recorcinol; In tetrahydrofuran; 1,4-dioxane; methanol; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm000558h

upstream raw materials:

N-(tert-butoxycarbonyl)-1,4-phenylenediamine

7-benzyloxy-3,4-dihydro-3-hydroxy-4-(3,4,5-trimethoxyphenyl)-3-isocoumarincarboxylic acid

N,N-dimethyl(3,4,5-trimethoxyphenyl)carboxamide

5-(benzyloxy)-2-bromobenzaldehyde dimethylacetal

Downstream raw materials:

7-benzyloxy-2-[(4-tert-butoxycarbonylamino)phenyl]-1,2-dihydro-N,N-dimethyl-1-oxo-4-(3,4,5-trimethoxyphenyl)-3-isoquinolinecarboxamide

7-benzyloxy-2-[(4-tert-butoxycarbonylamino)phenyl]-1,2-dihydro-N-methyl-1-oxo-4-(3,4,5-trimethoxyphenyl)-3-isoquinolinecarboxamide

methyl 7-benzyloxy-2-[(4-tert-butoxycarbonylamino)phenyl]-1,2-dihydro-1-oxo-4-(3,4,5-trimethoxyphenyl)-3-isoquinolinecarboxylate

2-(((2-(4-((tert-butoxycarbonyl)amino)phenyl)-3-(methoxycarbonyl)-1-oxo-4-(3,4,5-trimethoxyphenyl)-1,2-dihydroisoquinolin-7-yl)oxy)methyl)pyridine 1-oxide

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