3-((benzyl)(methylaminocarbonyl)methylaminocarbonyl)N-hydroxy-5-methylhexanamide

Base Information

• Chemical Name: 3-((benzyl)(methylaminocarbonyl)methylaminocarbonyl)N-hydroxy-5-methylhexanamide
• CAS No.: 108383-58-0
• Molecular Formula: C₁₈H₂₇N₃O₄
• Molecular Weight: 349.43
• Mol file: 108383-58-0.mol

Synonyms:Butanediamide,N4-hydroxy-N1-[2-(methylamino)-2-oxo-1-(phenylmethyl)ethyl]-2-(2-methylpropyl)-,[S-(R*,S*)]-; PNU 99533

Chemical Property of 3-((benzyl)(methylaminocarbonyl)methylaminocarbonyl)N-hydroxy-5-methylhexanamide

Chemical Property:

• PSA: 107.53000
• Density: 1.15g/cm³
• LogP: 2.19040

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-((benzyl)(methylaminocarbonyl)methylaminocarbonyl)N-hydroxy-5-methylhexanamide

There total 9 articles about 3-((benzyl)(methylaminocarbonyl)methylaminocarbonyl)N-hydroxy-5-methylhexanamide 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: 20.0%

(R)-5-Methyl-3-((S)-1-methylcarbamoyl-2-phenyl-ethylcarbamoyl)-hexanoic acid methyl ester (200866-05-3) → (R)-N4-Hydroxy-2-isobutyl-N1-((S)-1-methylcarbamoyl-2-phenyl-ethyl)-succinamide (108383-58-0)

Guidance literature:

With potassium hydroxide; hydroxylamine hydrochloride; In methanol; Ambient temperature;

DOI:10.1021/jm970494j

Reference yield:

2-methyl-2-propen-1-yl succinic anhydride (18908-20-8) → (R)-N4-Hydroxy-2-isobutyl-N1-((S)-1-methylcarbamoyl-2-phenyl-ethyl)-succinamide (108383-58-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 97.6 percent / H₂ / 10percent Pd/C / toluene / 14 h / 60 - 70 °C / 3102.9 Torr

2: 55.9 percent / 192 h / Ambient temperature

3: 64 percent / diethyl ether / 24 h / Ambient temperature

4: 98 percent / 1 N HCl / CHCl₃

5: 1.) CDI, 2.) Et₃N / 1.) THF, RT, 2 h, 2.) THF, RT

6: 20 percent / KOH, HONH₂*HCl / methanol / Ambient temperature

With hydrogenchloride; potassium hydroxide; hydroxylamine hydrochloride; hydrogen; triethylamine; 1,1'-carbonyldiimidazole; palladium on activated charcoal; In methanol; diethyl ether; chloroform; toluene;

DOI:10.1021/jm970494j

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → (R)-N4-Hydroxy-2-isobutyl-N1-((S)-1-methylcarbamoyl-2-phenyl-ethyl)-succinamide (108383-58-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) CDI / 1.) THF, RT, 2 h, 2.) THF, RT, 24 h

2: 100 percent / 4 N HCl / dioxane; methanol / 4 h / Ambient temperature

3: 1.) CDI, 2.) Et₃N / 1.) THF, RT, 2 h, 2.) THF, RT

4: 20 percent / KOH, HONH₂*HCl / methanol / Ambient temperature

With hydrogenchloride; potassium hydroxide; hydroxylamine hydrochloride; triethylamine; 1,1'-carbonyldiimidazole; In 1,4-dioxane; methanol;

DOI:10.1021/jm970494j

upstream raw materials:

(R)-5-Methyl-3-((S)-1-methylcarbamoyl-2-phenyl-ethylcarbamoyl)-hexanoic acid methyl ester

2-methyl-2-propen-1-yl succinic anhydride

N-tert-butoxycarbonyl-L-phenylalanine

L-phenylalanine methylamide hydrochloride

Refernces