ethyl N-({4-[(1R,2S)-1-(4-chlorophenyl)-1-{7-fluoro-5-methyl-1-[(4-nitrophenyl)sulfonyl]-1H-indol-3-yl}pentan-2-yl]phenyl}carbonyl)-β-alaninate

Base Information

• Chemical Name: ethyl N-({4-[(1R,2S)-1-(4-chlorophenyl)-1-{7-fluoro-5-methyl-1-[(4-nitrophenyl)sulfonyl]-1H-indol-3-yl}pentan-2-yl]phenyl}carbonyl)-β-alaninate
• CAS No.: 1403878-69-2
• Molecular Formula: C₃₈H₃₇ClFN₃O₇S
• Molecular Weight: 734.245
• Mol file: 1403878-69-2.mol

Synonyms:

Chemical Property of ethyl N-({4-[(1R,2S)-1-(4-chlorophenyl)-1-{7-fluoro-5-methyl-1-[(4-nitrophenyl)sulfonyl]-1H-indol-3-yl}pentan-2-yl]phenyl}carbonyl)-β-alaninate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl N-({4-[(1R,2S)-1-(4-chlorophenyl)-1-{7-fluoro-5-methyl-1-[(4-nitrophenyl)sulfonyl]-1H-indol-3-yl}pentan-2-yl]phenyl}carbonyl)-β-alaninate

There total 19 articles about ethyl N-({4-[(1R,2S)-1-(4-chlorophenyl)-1-{7-fluoro-5-methyl-1-[(4-nitrophenyl)sulfonyl]-1H-indol-3-yl}pentan-2-yl]phenyl}carbonyl)-β-alaninate 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:

2-fluoro-4-methylaniline (452-80-2) → ethyl N-({4-[(1R,2S)-1-(4-chlorophenyl)-1-{7-fluoro-5-methyl-1-[(4-nitrophenyl)sulfonyl]-1H-indol-3-yl}pentan-2-yl]phenyl}carbonyl)-β-alaninate (1403878-69-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: aluminum (III) chloride; boron trichloride; sodium hydroxide / dichloromethane; water / 14 h / Inert atmosphere; Reflux

2.1: sodium tetrahydroborate / water; pentan-1-ol / 2.42 h / 20 °C / Reflux

3.1: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / toluene / 15 °C

3.2: 20 °C

4.1: boron trifluoride diethyl etherate / dichloromethane / 22 °C

5.1: tetrahydrofuran / 1 h / 40 °C / Inert atmosphere

6.1: tetrahydrofuran / 1.4 h / 60 °C

With aluminum (III) chloride; sodium tetrahydroborate; boron trifluoride diethyl etherate; tetra(n-butyl)ammonium hydrogensulfate; boron trichloride; sodium hydroxide; In tetrahydrofuran; dichloromethane; pentan-1-ol; water; toluene;

DOI:10.1021/op300249q

Reference yield:

2-fluoro-4-methyl-6-((trimethylsilyl)ethynyl)aniline → ethyl N-({4-[(1R,2S)-1-(4-chlorophenyl)-1-{7-fluoro-5-methyl-1-[(4-nitrophenyl)sulfonyl]-1H-indol-3-yl}pentan-2-yl]phenyl}carbonyl)-β-alaninate (1403878-69-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: copper(l) iodide / N,N-dimethyl-formamide / 100 °C

2.1: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / toluene / 15 °C

2.2: 20 °C

3.1: boron trifluoride diethyl etherate / 1,2-dichloro-ethane / 5 - 22 °C

4.1: tetrahydrofuran / 1 h / 40 °C / Inert atmosphere

5.1: tetrahydrofuran / 1.4 h / 60 °C

With copper(l) iodide; boron trifluoride diethyl etherate; tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide; In tetrahydrofuran; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/op300249q

Reference yield:

7-fluoro-5-methyl-2-(trimethylsilyl)-1H-indole (1403878-67-0) → ethyl N-({4-[(1R,2S)-1-(4-chlorophenyl)-1-{7-fluoro-5-methyl-1-[(4-nitrophenyl)sulfonyl]-1H-indol-3-yl}pentan-2-yl]phenyl}carbonyl)-β-alaninate (1403878-69-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: trifluoroacetic acid / methanol; toluene; tetrahydrofuran / 5 h / 30 - 85 °C

2.1: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / toluene / 15 °C

2.2: 20 °C

3.1: methanesulfonic acid / trifluoroacetic acid / 20 h / 22 °C

4.1: tetrahydrofuran / 1 h / 40 °C / Inert atmosphere

5.1: tetrahydrofuran / 1.4 h / 60 °C

With methanesulfonic acid; tetra(n-butyl)ammonium hydrogensulfate; trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; methanol; toluene; trifluoroacetic acid; 3.1: |Friedel-Crafts Alkylation;

DOI:10.1021/op300249q

upstream raw materials:

4-chlorobenzoyl chloride

tert-butyl-4-bromobenzoate

2-fluoro-4-methylaniline

7-fluoro-5-methyl-2-(trimethylsilyl)-1H-indole