3-((E)-2-(methyl((1R)-1-(methyl((1R)-1-(methylcarbamoyl)-2-phenylethyl)carbamoyl)-2-(2-naphthyl)ethyl)carbamoyl)vinyl)azetidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 3-((E)-2-(methyl((1R)-1-(methyl((1R)-1-(methylcarbamoyl)-2-phenylethyl)carbamoyl)-2-(2-naphthyl)ethyl)carbamoyl)vinyl)azetidine-1-carboxylic acid tert-butyl ester
• CAS No.: 193085-23-3
• Molecular Formula: C₃₆H₄₄N₄O₅
• Molecular Weight: 612.769

Synonyms:3-((E)-2-(methyl((1R)-1-(methyl((1R)-1-(methylcarbamoyl)-2-phenylethyl)carbamoyl)-2-(2-naphthyl)ethyl)carbamoyl)vinyl)azetidine-1-carboxylic acid tert-butyl ester

Chemical Property of 3-((E)-2-(methyl((1R)-1-(methyl((1R)-1-(methylcarbamoyl)-2-phenylethyl)carbamoyl)-2-(2-naphthyl)ethyl)carbamoyl)vinyl)azetidine-1-carboxylic acid tert-butyl ester

Chemical Property:

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Technology Process of 3-((E)-2-(methyl((1R)-1-(methyl((1R)-1-(methylcarbamoyl)-2-phenylethyl)carbamoyl)-2-(2-naphthyl)ethyl)carbamoyl)vinyl)azetidine-1-carboxylic acid tert-butyl ester

There total 7 articles about 3-((E)-2-(methyl((1R)-1-(methyl((1R)-1-(methylcarbamoyl)-2-phenylethyl)carbamoyl)-2-(2-naphthyl)ethyl)carbamoyl)vinyl)azetidine-1-carboxylic 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:

tert-butyl 3-formylazetidine-1-carboxylate (177947-96-5) → 3-((E)-2-(methyl((1R)-1-(methyl((1R)-1-(methylcarbamoyl)-2-phenylethyl)carbamoyl)-2-(2-naphthyl)ethyl)carbamoyl)vinyl)azetidine-1-carboxylic acid tert-butyl ester (193085-23-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1.0 g / KOtBu / tetrahydrofuran / 1 h / 20 °C

2.1: 0.76 g / aq. LiOH / dioxane / 12 h / 20 °C

3.1: 1-hydroxy-7-azabenzotriazole; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride / CH₂Cl₂; dimethylformamide

3.2: iPr₂NEt / CH₂Cl₂; dimethylformamide

With lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; potassium tert-butylate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; 1.1: Wittig-Horner olefination / 2.1: Hydrolysis / 3.1: Esterification / 3.2: Acylation;

DOI:10.1016/S0223-5234(99)80086-5

Reference yield:

3-ethoxycarbonyloxycarbonyl-azetidine-1-carboxylic acid tert-butyl ester → 3-((E)-2-(methyl((1R)-1-(methyl((1R)-1-(methylcarbamoyl)-2-phenylethyl)carbamoyl)-2-(2-naphthyl)ethyl)carbamoyl)vinyl)azetidine-1-carboxylic acid tert-butyl ester (193085-23-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: LiBH₄ / tetrahydrofuran / 12 h / 20 °C

2.1: 1.11 g / oxalyl chloride; DMSO; NEt₃ / CH₂Cl₂ / -78 - 20 °C

3.1: 1.0 g / KOtBu / tetrahydrofuran / 1 h / 20 °C

4.1: 0.76 g / aq. LiOH / dioxane / 12 h / 20 °C

5.1: 1-hydroxy-7-azabenzotriazole; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride / CH₂Cl₂; dimethylformamide

5.2: iPr₂NEt / CH₂Cl₂; dimethylformamide

With lithium hydroxide; lithium borohydride; 1-hydroxy-7-aza-benzotriazole; oxalyl dichloride; potassium tert-butylate; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; 1.1: Reduction / 2.1: Swern oxidation / 3.1: Wittig-Horner olefination / 4.1: Hydrolysis / 5.1: Esterification / 5.2: Acylation;

DOI:10.1016/S0223-5234(99)80086-5

Reference yield:

3-((E)-2-ethoxycarbonylvinyl)azetidine-1-carboxylic acid tert-butyl ester (193085-21-1) → 3-((E)-2-(methyl((1R)-1-(methyl((1R)-1-(methylcarbamoyl)-2-phenylethyl)carbamoyl)-2-(2-naphthyl)ethyl)carbamoyl)vinyl)azetidine-1-carboxylic acid tert-butyl ester (193085-23-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 0.76 g / aq. LiOH / dioxane / 12 h / 20 °C

2.1: 1-hydroxy-7-azabenzotriazole; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride / CH₂Cl₂; dimethylformamide

2.2: iPr₂NEt / CH₂Cl₂; dimethylformamide

With lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; 1.1: Hydrolysis / 2.1: Esterification / 2.2: Acylation;

DOI:10.1016/S0223-5234(99)80086-5

upstream raw materials:

3-((E)-2-carboxyvinyl)azetidine-1-carboxylic acid tert-butyl ester

(2R)-N-Methyl-2-methylamino-N-((1R)-1-(methylcarbamoyl)-2-phenylethyl)-3-(2-naphthyl)propionamide

tert-butyl 3-formylazetidine-1-carboxylate

3-((E)-2-ethoxycarbonylvinyl)azetidine-1-carboxylic acid tert-butyl ester

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