((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

Base Information

• Chemical Name: ((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
• CAS No.: 202811-48-1
• Molecular Formula: C₃₈H₅₁N₃O₆
• Molecular Weight: 645.839

Synonyms:((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

Chemical Property of ((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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Technology Process of ((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

There total 10 articles about ((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 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:

(2E)-5-(tert-butyloxycarbonylamino)-5-methylhex-2-enoic acid (181646-42-4) + (2R)-N-(2-(2-(3-hydroxypropoxy)phenyl)ethyl)-N-methyl-2-(methylamino)-3-(2-naphthyl)propionamide (202811-47-0) → ((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 (202811-48-1)

Guidance literature:

(2E)-5-(tert-butyloxycarbonylamino)-5-methylhex-2-enoic acid; With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 ℃;

(2R)-N-(2-(2-(3-hydroxypropoxy)phenyl)ethyl)-N-methyl-2-(methylamino)-3-(2-naphthyl)propionamide; With N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃;

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

Reference yield:

2-hydroxyphenylacetic acid benzyl ether (22047-88-7) → ((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 (202811-48-1)

Guidance literature:

Multi-step reaction with 9 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

9.1: 1-hydroxy-7-azabenzotriazole; N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 0 °C

9.2: iPr₂NEt / CH₂Cl₂; dimethylformamide / 0 - 20 °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 / 9.1: Addition / 9.2: Condensation;

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

Reference yield:

N-(2-(2-benzyloxyphenyl)ethyl)-N-methylamine (202811-41-4) → ((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 (202811-48-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 88 percent / aq. NaOH / tetrahydrofuran / 16 h / 20 °C

2.1: 83 percent / H₂ / 10 percent Pd-C / ethanol / 16 h / 760 Torr

3.1: 70 percent / K₂CO₃; CsCl / dimethylformamide / 16 h / 80 °C

4.1: CF₃COOH / CH₂Cl₂ / 30 h / 0 °C

5.1: 1-hydroxy-7-azabenzotriazole; N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride / CH₂Cl₂; dimethylformamide / 0 °C

5.2: CH₂Cl₂; dimethylformamide / 0 - 20 °C

6.1: CF₃COOH / CH₂Cl₂ / 0 °C

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

7.2: iPr₂NEt / CH₂Cl₂; dimethylformamide / 0 - 20 °C

With sodium hydroxide; 1-hydroxy-7-aza-benzotriazole; cesium chloride; hydrogen; 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: Substitution / 2.1: Catalytic hydrogenation / 3.1: Alkylation / 4.1: solvolysis / 5.1: Addition / 5.2: Condensation / 6.1: solvolysis / 7.1: Addition / 7.2: Condensation;

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

upstream raw materials:

(2E)-5-(tert-butyloxycarbonylamino)-5-methylhex-2-enoic acid

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

2-hydroxyphenylacetic acid benzyl ether

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

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