2-((S)-2-((R)-2-(3,4-dichlorophenyl)-5-hydroxy-N-methylpentanamido)-3-phenylpropanamido)-ethyl carbamic acid benzylester

Base Information

• Chemical Name: 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-5-hydroxy-N-methylpentanamido)-3-phenylpropanamido)-ethyl carbamic acid benzylester
• CAS No.: 1563182-79-5
• Molecular Formula: C₃₁H₃₅Cl₂N₃O₅
• Molecular Weight: 600.542

Synonyms:2-((S)-2-((R)-2-(3,4-dichlorophenyl)-5-hydroxy-N-methylpentanamido)-3-phenylpropanamido)-ethyl carbamic acid benzylester

Chemical Property of 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-5-hydroxy-N-methylpentanamido)-3-phenylpropanamido)-ethyl carbamic acid benzylester

Chemical Property:

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Technology Process of 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-5-hydroxy-N-methylpentanamido)-3-phenylpropanamido)-ethyl carbamic acid benzylester

There total 12 articles about 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-5-hydroxy-N-methylpentanamido)-3-phenylpropanamido)-ethyl carbamic acid benzylester 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: 99.0%

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-((R)-2-(3,4-dichlorophenyl)-5-hydroxy-N-methylpentanamido)-3-phenylpropanamido)-ethyl carbamic acid benzylester (1563182-79-5)

Guidance literature:

2-((S)-2-((R)-2-(3,4-dichlorophenyl)-N-methylpent-4-enamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester; With Wilkinson's catalyst; benzo[1,3,2]dioxaborole; In tetrahydrofuran; at 0 - 20 ℃; for 6.5h; Inert atmosphere;

With dihydrogen peroxide; In tetrahydrofuran; aq. phosphate buffer; ethanol; at 0 - 20 ℃; for 12h; regioselective reaction;

DOI:10.1021/ml400528y

Reference yield: 98.0%

2-((S)-2-((S)-2-(3,4-dichlorophenyl)-N-methylpent-4-enamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester (1563182-66-0) → 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-5-hydroxy-N-methylpentanamido)-3-phenylpropanamido)-ethyl carbamic acid benzylester (1563182-79-5)

Guidance literature:

2-((S)-2-((S)-2-(3,4-dichlorophenyl)-N-methylpent-4-enamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester; With Wilkinson's catalyst; benzo[1,3,2]dioxaborole; In tetrahydrofuran; at 0 - 20 ℃; for 6.5h; Inert atmosphere;

With dihydrogen peroxide; In tetrahydrofuran; aq. phosphate buffer; ethanol; at 0 - 20 ℃; for 12h; regioselective reaction;

DOI:10.1021/ml400528y

Reference yield:

(S)-N-benzyloxycarbonyl-N-methyl-phenyl alanine (2899-07-2) → 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-5-hydroxy-N-methylpentanamido)-3-phenylpropanamido)-ethyl carbamic acid benzylester (1563182-79-5)

Guidance literature:

Multi-step reaction with 6 steps

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

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

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

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

5.1: 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.08 h / 0 °C / Inert atmosphere

5.2: 16 h / 20 °C / Inert atmosphere

6.1: Wilkinson's catalyst; benzo[1,3,2]dioxaborole / tetrahydrofuran / 6.5 h / 0 - 20 °C / Inert atmosphere

6.2: 12 h / 0 - 20 °C

With hydrogenchloride; Wilkinson's catalyst; palladium 10% on activated carbon; hydrogen; benzotriazol-1-ol; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; benzo[1,3,2]dioxaborole; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;

DOI:10.1021/ml400528y

upstream raw materials:

N-Cbz-L-Phe

(S)-N-benzyloxycarbonyl-N-methyl-phenyl alanine

3,4-dichlorophenyl acetic acid

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

Downstream raw materials:

2-((S)-2-((R)-2-(3,4-dichlorophenyl)-5-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-N-methylpentanamido)-3-phenylpropanamido)ethylcarbamic acid benzyl ester

2-((S)-2-((R)-2-(3,4-dichlorophenyl)-N-methyl-5-oxopentanamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester

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