(S)-N-{[5-{[(4-methylphenyl)sulfonyl]amino}-3-(trifluoroacetyl)-1H-indol-1-yl]acetyl}-L-leucine

Base Information

• Chemical Name: (S)-N-{[5-{[(4-methylphenyl)sulfonyl]amino}-3-(trifluoroacetyl)-1H-indol-1-yl]acetyl}-L-leucine
• CAS No.: 1623002-61-8
• Molecular Formula: C₂₅H₂₆F₃N₃O₆S
• Molecular Weight: 553.559

Synonyms:

Chemical Property of (S)-N-{[5-{[(4-methylphenyl)sulfonyl]amino}-3-(trifluoroacetyl)-1H-indol-1-yl]acetyl}-L-leucine

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

NTRC824 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: NTRC 824 is a potent and selective non-peptide neurotensin (NTS) type-2 receptor antagonist.

Technology Process of (S)-N-{[5-{[(4-methylphenyl)sulfonyl]amino}-3-(trifluoroacetyl)-1H-indol-1-yl]acetyl}-L-leucine

There total 6 articles about (S)-N-{[5-{[(4-methylphenyl)sulfonyl]amino}-3-(trifluoroacetyl)-1H-indol-1-yl]acetyl}-L-leucine 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: 86.0%

(S)-tert-butyl N-{[5-{[(4-methylphenyl)sulfonyl]amino}-3-(trifluoroacetyl)-1H-indol-1-yl]acetyl}-L-leucinate → (S)-N-{[5-{[(4-methylphenyl)sulfonyl]amino}-3-(trifluoroacetyl)-1H-indol-1-yl]acetyl}-L-leucine (1623002-61-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jm500857r

Reference yield:

(5-nitro-1H-indol-1-yl)acetic acid (226901-50-4) → (S)-N-{[5-{[(4-methylphenyl)sulfonyl]amino}-3-(trifluoroacetyl)-1H-indol-1-yl]acetyl}-L-leucine (1623002-61-8)

Guidance literature:

Multi-step reaction with 5 steps

1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine / dichloromethane / 4 h / 20 °C / Inert atmosphere

2: hydrogen; palladium 10% on activated carbon / ethanol / 2 h / 20 °C / 2828.7 Torr / Inert atmosphere

3: dmap / dichloromethane / 16 h / 20 °C / Inert atmosphere

4: dichloromethane / 20 °C / Inert atmosphere

5: trifluoroacetic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere

With dmap; palladium 10% on activated carbon; hydrogen; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; trifluoroacetic acid; In ethanol; dichloromethane;

DOI:10.1021/jm500857r

Reference yield:

5-nitroindole (6146-52-7) → (S)-N-{[5-{[(4-methylphenyl)sulfonyl]amino}-3-(trifluoroacetyl)-1H-indol-1-yl]acetyl}-L-leucine (1623002-61-8)

Guidance literature:

Multi-step reaction with 7 steps

1: potassium carbonate / acetone / 96 h / 20 °C / Inert atmosphere

2: lithium hydroxide; water / 1,4-dioxane / 16 h / 20 °C / Inert atmosphere

3: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine / dichloromethane / 4 h / 20 °C / Inert atmosphere

4: hydrogen; palladium 10% on activated carbon / ethanol / 2 h / 20 °C / 2828.7 Torr / Inert atmosphere

5: dmap / dichloromethane / 16 h / 20 °C / Inert atmosphere

6: dichloromethane / 20 °C / Inert atmosphere

7: trifluoroacetic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere

With dmap; palladium 10% on activated carbon; water; hydrogen; potassium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; trifluoroacetic acid; lithium hydroxide; In 1,4-dioxane; ethanol; dichloromethane; acetone;

DOI:10.1021/jm500857r

upstream raw materials:

methyl 2-(5-nitro-1H-indol-1-yl)acetate

(5-nitro-1H-indol-1-yl)acetic acid

5-nitroindole

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