tert-butyl 2-((R)-2-((R)-2-(3,4-dichlorophenyl)-N,2-dimethyl-4-oxobutanamido)-3-phenylpropanamido)ethylcarbamate

Base Information

• Chemical Name: tert-butyl 2-((R)-2-((R)-2-(3,4-dichlorophenyl)-N,2-dimethyl-4-oxobutanamido)-3-phenylpropanamido)ethylcarbamate
• CAS No.: 1563183-32-3
• Molecular Formula: C₂₈H₃₅Cl₂N₃O₅
• Molecular Weight: 564.509

Synonyms:tert-butyl 2-((R)-2-((R)-2-(3,4-dichlorophenyl)-N,2-dimethyl-4-oxobutanamido)-3-phenylpropanamido)ethylcarbamate

Chemical Property of tert-butyl 2-((R)-2-((R)-2-(3,4-dichlorophenyl)-N,2-dimethyl-4-oxobutanamido)-3-phenylpropanamido)ethylcarbamate

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Technology Process of tert-butyl 2-((R)-2-((R)-2-(3,4-dichlorophenyl)-N,2-dimethyl-4-oxobutanamido)-3-phenylpropanamido)ethylcarbamate

There total 7 articles about tert-butyl 2-((R)-2-((R)-2-(3,4-dichlorophenyl)-N,2-dimethyl-4-oxobutanamido)-3-phenylpropanamido)ethylcarbamate 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 2-((R)-2-((R)-2-(3,4-dichlorophenyl)-N,2-dimethylpent-4-enamido)-3-phenylpropanamido)ethylcarbamate (1563183-30-1) → tert-butyl 2-((R)-2-((R)-2-(3,4-dichlorophenyl)-N,2-dimethyl-4-oxobutanamido)-3-phenylpropanamido)ethylcarbamate (1563183-32-3)

Guidance literature:

With sodium periodate; osmium(VIII) oxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; at 20 ℃; for 12h; Darkness;

DOI:10.1021/ml400528y

Reference yield:

3,4-dichlorophenyl acetic acid (5807-30-7) → tert-butyl 2-((R)-2-((R)-2-(3,4-dichlorophenyl)-N,2-dimethyl-4-oxobutanamido)-3-phenylpropanamido)ethylcarbamate (1563183-32-3)

Guidance literature:

Multi-step reaction with 8 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: thionyl chloride / 11.33 h / 20 °C / Inert atmosphere; Cooling with ice

3.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 5 h / 0 - 20 °C / Inert atmosphere

3.2: 2 h / 20 °C / Inert atmosphere

4.1: lithium hydroxide; water / methanol / 10 h / Reflux

5.1: ethyl acetate / Resolution of racemate; Inert atmosphere

6.1: hydrogenchloride / ethyl acetate; water

7.1: thionyl chloride / benzene / 12 h / Reflux; Inert atmosphere

7.2: 6 h / 20 °C / Inert atmosphere

8.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide; sodium periodate / tetrahydrofuran; water / 12 h / 20 °C / Darkness

With hydrogenchloride; sodium periodate; osmium(VIII) oxide; thionyl chloride; water; sodium hydride; 4-methylmorpholine N-oxide; lithium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; water; ethyl acetate; N,N-dimethyl-formamide; mineral oil; pentane; benzene;

DOI:10.1021/ml400528y

Reference yield:

2-(S)-(3,4-dichloro-phenyl)-4-pentenoic acid (79333-48-5) → tert-butyl 2-((R)-2-((R)-2-(3,4-dichlorophenyl)-N,2-dimethyl-4-oxobutanamido)-3-phenylpropanamido)ethylcarbamate (1563183-32-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: thionyl chloride / 11.33 h / 20 °C / Inert atmosphere; Cooling with ice

2.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 5 h / 0 - 20 °C / Inert atmosphere

2.2: 2 h / 20 °C / Inert atmosphere

3.1: lithium hydroxide; water / methanol / 10 h / Reflux

4.1: ethyl acetate / Resolution of racemate; Inert atmosphere

5.1: hydrogenchloride / ethyl acetate; water

6.1: thionyl chloride / benzene / 12 h / Reflux; Inert atmosphere

6.2: 6 h / 20 °C / Inert atmosphere

7.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide; sodium periodate / tetrahydrofuran; water / 12 h / 20 °C / Darkness

With hydrogenchloride; sodium periodate; osmium(VIII) oxide; thionyl chloride; water; sodium hydride; 4-methylmorpholine N-oxide; lithium hydroxide; In tetrahydrofuran; methanol; water; ethyl acetate; N,N-dimethyl-formamide; mineral oil; benzene;

DOI:10.1021/ml400528y

upstream raw materials:

3,4-dichlorophenyl acetic acid

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

2-(3,4-dichloro-phenyl)-pent-4-enoic acid methyl ester

C₈H₁₁N*C₁₂H₁₂Cl₂O₂

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