N-[2-(3-benzyloxy-4,5-dimethoxy-phenyl)-ethyl]-2-[4-(5-formyl-2-isopropoxy-phenoxy)-phenyl]-N-(1-phenyl-ethyl)-acetamide

Base Information

• Chemical Name: N-[2-(3-benzyloxy-4,5-dimethoxy-phenyl)-ethyl]-2-[4-(5-formyl-2-isopropoxy-phenoxy)-phenyl]-N-(1-phenyl-ethyl)-acetamide
• CAS No.: 454186-00-6
• Molecular Formula: C₄₃H₄₅NO₇
• Molecular Weight: 687.833

Synonyms:N-[2-(3-benzyloxy-4,5-dimethoxy-phenyl)-ethyl]-2-[4-(5-formyl-2-isopropoxy-phenoxy)-phenyl]-N-(1-phenyl-ethyl)-acetamide

Chemical Property of N-[2-(3-benzyloxy-4,5-dimethoxy-phenyl)-ethyl]-2-[4-(5-formyl-2-isopropoxy-phenoxy)-phenyl]-N-(1-phenyl-ethyl)-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[2-(3-benzyloxy-4,5-dimethoxy-phenyl)-ethyl]-2-[4-(5-formyl-2-isopropoxy-phenoxy)-phenyl]-N-(1-phenyl-ethyl)-acetamide

There total 27 articles about N-[2-(3-benzyloxy-4,5-dimethoxy-phenyl)-ethyl]-2-[4-(5-formyl-2-isopropoxy-phenoxy)-phenyl]-N-(1-phenyl-ethyl)-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:

Methyl 4-hydroxyphenylacetate (14199-15-6) → N-[2-(3-benzyloxy-4,5-dimethoxy-phenyl)-ethyl]-2-[4-(5-formyl-2-isopropoxy-phenoxy)-phenyl]-N-(1-phenyl-ethyl)-acetamide (454186-00-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / -40 °C

2.1: 85 percent / potassium acetate; PdCl₂(dppf) / dioxane / 80 °C

3.1: diethanolamine / propan-2-ol; diethyl ether

3.2: hydrochloric acid / H₂O; tetrahydrofuran / 20 °C

4.1: 57 percent / copper(II) acetate; pyridine; molecular sieves 4 Angstroem / CH₂Cl₂ / 48 h / 20 °C

5.1: 100 percent / lithium hydroxide / methanol; tetrahydrofuran; H₂O / 2 h / 20 °C

6.1: 73 percent / 1-hydroxybenzotriazole hydrate; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide / 48 h / 0 °C

7.1: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 0 °C

8.1: Dess-Martin periodinane / 1 h

With pyridine; 2,6-dimethylpyridine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; lithium hydroxide; 4 A molecular sieve; tetrabutyl ammonium fluoride; potassium acetate; copper diacetate; Dess-Martin periodane; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 2,2'-iminobis[ethanol]; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; 8.1: Dess-Martin oxidation;

DOI:10.1021/ol0261635

Reference yield:

3-bromo-4-hydroxybenzylaldehyde (2973-78-6) → N-[2-(3-benzyloxy-4,5-dimethoxy-phenyl)-ethyl]-2-[4-(5-formyl-2-isopropoxy-phenoxy)-phenyl]-N-(1-phenyl-ethyl)-acetamide (454186-00-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 94 percent / potassium carbonate / dimethylsulfoxide / 12 h / 55 °C

2.1: 98 percent / sodium borohydride / tetrahydrofuran; methanol / 2 h / 20 °C

3.1: 95 percent / imidazole / dimethylformamide / 12 h / 20 °C

4.1: n-butyllithium / tetrahydrofuran / 12 h / -78 - 20 °C

4.2: 82 percent / hydrogen peroxide / tetrahydrofuran / 24 h / 20 °C

5.1: 57 percent / copper(II) acetate; pyridine; molecular sieves 4 Angstroem / CH₂Cl₂ / 48 h / 20 °C

6.1: 100 percent / lithium hydroxide / methanol; tetrahydrofuran; H₂O / 2 h / 20 °C

7.1: 73 percent / 1-hydroxybenzotriazole hydrate; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide / 48 h / 0 °C

8.1: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 0 °C

9.1: Dess-Martin periodinane / 1 h

With pyridine; 1H-imidazole; lithium hydroxide; sodium tetrahydroborate; n-butyllithium; 4 A molecular sieve; tetrabutyl ammonium fluoride; copper diacetate; potassium carbonate; Dess-Martin periodane; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 9.1: Dess-Martin oxidation;

DOI:10.1021/ol0261635

Reference yield:

(3-bromo-4,5-dimethoxyphenyl)methanol (52783-74-1) → N-[2-(3-benzyloxy-4,5-dimethoxy-phenyl)-ethyl]-2-[4-(5-formyl-2-isopropoxy-phenoxy)-phenyl]-N-(1-phenyl-ethyl)-acetamide (454186-00-6)

Guidance literature:

Multi-step reaction with 12 steps

1.1: imidazole / dimethylformamide / 12 h / 20 °C

2.1: n-butyllithium / 1 h / -78 °C

2.2: trimethyl borate / 12 h / -78 - 20 °C

2.3: 78 percent / hydrogen peroxide / 12 h / 20 °C

3.1: 75 percent / potassium carbonate / acetone / 12 h / Heating

4.1: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h / 0 °C

5.1: SOCl₂ / benzene / 12 h / 20 °C

5.2: dimethylsulfoxide; benzene / 20 °C

6.1: 98 percent / sodium hydroxide / ethanol / 20 h / Heating

7.1: oxalyl chloride / benzene / 2 h / 20 °C

8.1: sodium hydroxide / H₂O; CH₂Cl₂ / 1 h / 20 °C

9.1: B₂H₆*THF; BF₃*Et₂O / tetrahydrofuran / Heating

9.2: 98 percent / hydrochloric acid / H₂O; tetrahydrofuran

10.1: 73 percent / 1-hydroxybenzotriazole hydrate; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide / 48 h / 0 °C

11.1: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 0 °C

12.1: Dess-Martin periodinane / 1 h

With 1H-imidazole; sodium hydroxide; n-butyllithium; thionyl chloride; oxalyl dichloride; B₂H₆-THF; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; potassium carbonate; Dess-Martin periodane; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; benzene; 8.1: Schotten-Baumann reaction / 12.1: Dess-Martin oxidation;

DOI:10.1021/ol0261635

upstream raw materials:

N-[2-(3-benzyloxy-4,5-dimethoxy-phenyl)-ethyl]-2-[4-(5-hydroxymethyl-2-isopropoxy-phenoxy)-phenyl]-N-(1-phenyl-ethyl)-acetamide

3-benzyloxy-4,5-dimethoxybenzyl alcohol

5-bromo-4-hydroxy-3-methoxybenzaldehyde

Methyl 4-hydroxyphenylacetate

Downstream raw materials:

3-(4-{[[2-(3-Benzyloxy-4,5-dimethoxy-phenyl)-ethyl]-((S)-1-phenyl-ethyl)-carbamoyl]-methyl}-phenoxy)-4-isopropoxy-benzoic acid

8-hydroxy-1-[4-(2-isopropoxy-5-methoxycarbonyl-phenoxy)-benzyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

3-(4-{[[2-(3-Benzyloxy-4,5-dimethoxy-phenyl)-ethyl]-((S)-1-phenyl-ethyl)-carbamoyl]-methyl}-phenoxy)-4-isopropoxy-benzoic acid methyl ester

3-{4-[(S)-8-Benzyloxy-6,7-dimethoxy-2-((S)-1-phenyl-ethyl)-1,2,3,4-tetrahydro-isoquinolin-1-ylmethyl]-phenoxy}-4-isopropoxy-benzoic acid methyl ester

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