2-((S)-2-((R)-2-(3,4-dichlorophenyl)-N-methylpent-4-enamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester

Base Information

• Chemical Name: 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-N-methylpent-4-enamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester
• CAS No.: 1563182-65-9
• Molecular Formula: C₃₁H₃₃Cl₂N₃O₄
• Molecular Weight: 582.527

Synonyms:2-((S)-2-((R)-2-(3,4-dichlorophenyl)-N-methylpent-4-enamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester

Chemical Property of 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-N-methylpent-4-enamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-N-methylpent-4-enamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester

There total 5 articles about 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-N-methylpent-4-enamido)-3-phenylpropanamido)ethyl carbamic acid benzyl 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: 94.0%

(S)-benzyl 2-(2-(methylamino)-3-phenylpropanamido)ethylcarbamate (1563182-64-8) + 2-(S)-(3,4-dichloro-phenyl)-4-pentenoic acid (79333-48-5) → 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-N-methylpent-4-enamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester (1563182-65-9) + 2-((S)-2-((S)-2-(3,4-dichlorophenyl)-N-methylpent-4-enamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester (1563182-66-0)

Guidance literature:

2-(S)-(3,4-dichloro-phenyl)-4-pentenoic acid; With N-ethyl-N,N-diisopropylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; In tetrahydrofuran; at 0 ℃; for 0.0833333h; Inert atmosphere;

(S)-benzyl 2-(2-(methylamino)-3-phenylpropanamido)ethylcarbamate; In tetrahydrofuran; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1021/ml400528y

Reference yield:

N-Cbz-L-Phe (1161-13-3) → 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-N-methylpent-4-enamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester (1563182-65-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: (1S)-10-camphorsulfonic acid / toluene / 0.5 h / Reflux; Inert atmosphere

1.2: 3 h / 20 °C / Inert atmosphere

2.1: palladium 10% on activated carbon; hydrogen / methanol / 8 h / 20 °C

3.1: triethylamine / dichloromethane / 8 h / 0 - 20 °C / Inert atmosphere

4.1: triethylamine; benzotriazol-1-ol; dicyclohexyl-carbodiimide / dichloromethane / 20 °C / Cooling with ice; Inert atmosphere

5.1: hydrogenchloride / 1,4-dioxane / 10 h / 20 °C / Inert atmosphere

6.1: 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.08 h / 0 °C / Inert atmosphere

6.2: 16 h / 20 °C / Inert atmosphere

With hydrogenchloride; palladium 10% on activated carbon; (1S)-10-camphorsulfonic acid; hydrogen; benzotriazol-1-ol; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; toluene;

DOI:10.1021/ml400528y

Reference yield:

3,4-dichlorophenyl acetic acid (5807-30-7) → 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-N-methylpent-4-enamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester (1563182-65-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran; pentane / 2 h / -25 °C / Inert atmosphere

1.2: 1.27 h / -25 - 20 °C / Inert atmosphere

2.1: 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.08 h / 0 °C / Inert atmosphere

2.2: 16 h / 20 °C / Inert atmosphere

With N-ethyl-N,N-diisopropylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; lithium hexamethyldisilazane; In tetrahydrofuran; pentane;

DOI:10.1021/ml400528y

upstream raw materials:

N-Cbz-L-Phe

3,4-dichlorophenyl acetic acid

(S)-benzyl 2-(2-(methylamino)-3-phenylpropanamido)ethylcarbamate

2-(S)-(3,4-dichloro-phenyl)-4-pentenoic acid

Downstream raw materials:

2-((S)-2-((R)-2-(3,4-dichlorophenyl)-N-methylpent-4-oxobutanamido)-3-phenylpropanamido)ethylcarbamic acid benzyl ester

2-((S)-2-((R)-2-(3,4-dichlorophenyl)-N-methyl-4-(4-(N-propylmethylsulfonamido)piperidin-1-yl)butanamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester

2-((S)-2-((R)-2-(3,4-dichlorophenyl)-N-methyl-4-(1-methyl-2-oxospiro[indoline-3,4'-piperidine]-1'-yl)butanamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester

2-((S)-2-((R)-2-(3,4-dichlorophenyl)-4-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-N-methylbutanamido)-3-phenylpropanamido)ethylcarbamic acid benzyl ester

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