N¹-{1-[5-(5-amino-1-carbamoyl-pentylcarbamoyl)-pentylcarbamoyl]-2-phenyl-ethyl}-N⁴-hydroxy-2-isobutyl-succinamide

Base Information

• Chemical Name: N¹-{1-[5-(5-amino-1-carbamoyl-pentylcarbamoyl)-pentylcarbamoyl]-2-phenyl-ethyl}-N⁴-hydroxy-2-isobutyl-succinamide
• CAS No.: 886057-21-2
• Molecular Formula: C₂₉H₄₈N₆O₆
• Molecular Weight: 576.737

Synonyms:N¹-{1-[5-(5-amino-1-carbamoyl-pentylcarbamoyl)-pentylcarbamoyl]-2-phenyl-ethyl}-N⁴-hydroxy-2-isobutyl-succinamide

Chemical Property of N¹-{1-[5-(5-amino-1-carbamoyl-pentylcarbamoyl)-pentylcarbamoyl]-2-phenyl-ethyl}-N⁴-hydroxy-2-isobutyl-succinamide

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N¹-{1-[5-(5-amino-1-carbamoyl-pentylcarbamoyl)-pentylcarbamoyl]-2-phenyl-ethyl}-N⁴-hydroxy-2-isobutyl-succinamide

There total 7 articles about N¹-{1-[5-(5-amino-1-carbamoyl-pentylcarbamoyl)-pentylcarbamoyl]-2-phenyl-ethyl}-N⁴-hydroxy-2-isobutyl-succinamide 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: 53.0%

pentafluorophenyl 2-(R)-isobutyl-3-(N-tert-butoxycarbonyl-N-(tert-butyl-dimethylsilyloxy)carbamoyl)propionate (886057-13-2) + N-Fmoc L-Phe (35661-40-6) + Fmoc-Lys(tert-butoxycarbonyl) (71989-26-9) + 6-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}hexanoic acid (88574-06-5) → N1-{1-[5-(5-amino-1-carbamoyl-pentylcarbamoyl)-pentylcarbamoyl]-2-phenyl-ethyl}-N4-hydroxy-2-isobutyl-succinamide (886057-21-2)

Guidance literature:

Multistep reaction;

DOI:10.1021/ol060409e

Reference yield:

3-(R)-benzyloxycarbonyl-5-methylhexanoic acid chloride (151667-50-4) → N1-{1-[5-(5-amino-1-carbamoyl-pentylcarbamoyl)-pentylcarbamoyl]-2-phenyl-ethyl}-N4-hydroxy-2-isobutyl-succinamide (886057-21-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / DMAP / acetonitrile / 0 - 20 °C

2: hydrogen / Pd/C / methanol / 1.5 h

3: 0.87 g / N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide / CH₂Cl₂ / 20 °C

With dmap; hydrogen; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium on activated charcoal; In methanol; dichloromethane; acetonitrile;

DOI:10.1021/ol060409e

Reference yield:

tert-butyl 3-(R)-benzyloxycarbonyl-5-methylhexanoate (129739-13-5) → N1-{1-[5-(5-amino-1-carbamoyl-pentylcarbamoyl)-pentylcarbamoyl]-2-phenyl-ethyl}-N4-hydroxy-2-isobutyl-succinamide (886057-21-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 94 percent / TFA / CH₂Cl₂

2: oxalyl chloride / DMF / CH₂Cl₂ / 0.5 h / 20 °C

3: 85 percent / DMAP / acetonitrile / 0 - 20 °C

4: hydrogen / Pd/C / methanol / 1.5 h

5: 0.87 g / N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide / CH₂Cl₂ / 20 °C

With dmap; oxalyl dichloride; hydrogen; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; palladium on activated charcoal; N,N-dimethyl-formamide; In methanol; dichloromethane; acetonitrile;

DOI:10.1021/ol060409e

upstream raw materials:

pentafluorophenyl 2-(R)-isobutyl-3-(N-tert-butoxycarbonyl-N-(tert-butyl-dimethylsilyloxy)carbamoyl)propionate

N-Fmoc L-Phe

Fmoc-Lys(tert-butoxycarbonyl)

6-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}hexanoic acid

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