(2R)-N-(2-(2-(3-hydroxypropoxy)phenyl)ethyl)-N-methyl-2-(methylamino)-3-(2-naphthyl)propionamide

Base Information

• Chemical Name: (2R)-N-(2-(2-(3-hydroxypropoxy)phenyl)ethyl)-N-methyl-2-(methylamino)-3-(2-naphthyl)propionamide
• CAS No.: 202811-47-0
• Molecular Formula: C₂₆H₃₂N₂O₃
• Molecular Weight: 420.552

Synonyms:(2R)-N-(2-(2-(3-hydroxypropoxy)phenyl)ethyl)-N-methyl-2-(methylamino)-3-(2-naphthyl)propionamide

Chemical Property of (2R)-N-(2-(2-(3-hydroxypropoxy)phenyl)ethyl)-N-methyl-2-(methylamino)-3-(2-naphthyl)propionamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-N-(2-(2-(3-hydroxypropoxy)phenyl)ethyl)-N-methyl-2-(methylamino)-3-(2-naphthyl)propionamide

There total 9 articles about (2R)-N-(2-(2-(3-hydroxypropoxy)phenyl)ethyl)-N-methyl-2-(methylamino)-3-(2-naphthyl)propionamide 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:

N-[(1R)-1-(N-(2-[2-(3-hydroxypropoxy)phenyl]ethyl)-N-methylcarbamoyl)-2-(2-naphthyl)ethyl]-N-methylcarbamic acid tert-butyl ester (202811-46-9) → (2R)-N-(2-(2-(3-hydroxypropoxy)phenyl)ethyl)-N-methyl-2-(methylamino)-3-(2-naphthyl)propionamide (202811-47-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃;

DOI:10.1016/S0223-5234(00)00160-4

Reference yield:

2-hydroxyphenylacetic acid benzyl ether (22047-88-7) → (2R)-N-(2-(2-(3-hydroxypropoxy)phenyl)ethyl)-N-methyl-2-(methylamino)-3-(2-naphthyl)propionamide (202811-47-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 1-hydroxybenzotriazole; N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride / CH₂Cl₂; dimethylformamide / 0.33 h / 0 °C

1.2: 65 percent / CH₂Cl₂; dimethylformamide; ethanol / 16 h / 0 - 20 °C

2.1: 38 percent / NaBH₄; I₂ / tetrahydrofuran / 16 h / Heating

3.1: 88 percent / aq. NaOH / tetrahydrofuran / 16 h / 20 °C

4.1: 83 percent / H₂ / 10 percent Pd-C / ethanol / 16 h / 760 Torr

5.1: 70 percent / K₂CO₃; CsCl / dimethylformamide / 16 h / 80 °C

6.1: CF₃COOH / CH₂Cl₂ / 30 h / 0 °C

7.1: 1-hydroxy-7-azabenzotriazole; N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride / CH₂Cl₂; dimethylformamide / 0 °C

7.2: CH₂Cl₂; dimethylformamide / 0 - 20 °C

8.1: CF₃COOH / CH₂Cl₂ / 0 °C

With sodium hydroxide; sodium tetrahydroborate; 1-hydroxy-7-aza-benzotriazole; cesium chloride; hydrogen; iodine; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Addition / 1.2: Condensation / 2.1: Reduction / 3.1: Substitution / 4.1: Catalytic hydrogenation / 5.1: Alkylation / 6.1: solvolysis / 7.1: Addition / 7.2: Condensation / 8.1: solvolysis;

DOI:10.1016/S0223-5234(00)00160-4

Reference yield:

2-(2-benzyloxyphenyl)-N-methylacetamide (202811-40-3) → (2R)-N-(2-(2-(3-hydroxypropoxy)phenyl)ethyl)-N-methyl-2-(methylamino)-3-(2-naphthyl)propionamide (202811-47-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 38 percent / NaBH₄; I₂ / tetrahydrofuran / 16 h / Heating

2.1: 88 percent / aq. NaOH / tetrahydrofuran / 16 h / 20 °C

3.1: 83 percent / H₂ / 10 percent Pd-C / ethanol / 16 h / 760 Torr

4.1: 70 percent / K₂CO₃; CsCl / dimethylformamide / 16 h / 80 °C

5.1: CF₃COOH / CH₂Cl₂ / 30 h / 0 °C

6.1: 1-hydroxy-7-azabenzotriazole; N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride / CH₂Cl₂; dimethylformamide / 0 °C

6.2: CH₂Cl₂; dimethylformamide / 0 - 20 °C

7.1: CF₃COOH / CH₂Cl₂ / 0 °C

With sodium hydroxide; sodium tetrahydroborate; 1-hydroxy-7-aza-benzotriazole; cesium chloride; hydrogen; iodine; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Reduction / 2.1: Substitution / 3.1: Catalytic hydrogenation / 4.1: Alkylation / 5.1: solvolysis / 6.1: Addition / 6.2: Condensation / 7.1: solvolysis;

DOI:10.1016/S0223-5234(00)00160-4

upstream raw materials:

N-[(1R)-1-(N-(2-[2-(3-hydroxypropoxy)phenyl]ethyl)-N-methylcarbamoyl)-2-(2-naphthyl)ethyl]-N-methylcarbamic acid tert-butyl ester

2-hydroxyphenylacetic acid benzyl ether

(2R)-2-(N-(tert-butoxycarbonyl)-N-methylamino)-3-(2-naphthyl)-propionic acid

N-(2-(2-benzyloxyphenyl)ethyl)-N-methylamine

Downstream raw materials:

((3E)-4-N-((1R)-1-(N-(2-(2-(3-hydroxypropoxy)phenyl)ethyl)-N-methylcarbamoyl)-2-(2-naphthyl)ethyl)-N-methylcarbamoyl-1,1-dimethylbut-3-enyl)carbamic acid tert-butyl ester

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