(R)-5-Methyl-3-[((S)-methylcarbamoyl-phenyl-methyl)-carbamoyl]-2-methylene-hexanoic acid

Base Information

• Chemical Name: (R)-5-Methyl-3-[((S)-methylcarbamoyl-phenyl-methyl)-carbamoyl]-2-methylene-hexanoic acid
• CAS No.: 188729-12-6
• Molecular Formula: C₁₈H₂₄N₂O₄
• Molecular Weight: 332.4
• Mol file: 188729-12-6.mol

Synonyms:(R)-5-Methyl-3-[((S)-methylcarbamoyl-phenyl-methyl)-carbamoyl]-2-methylene-hexanoic acid

Chemical Property of (R)-5-Methyl-3-[((S)-methylcarbamoyl-phenyl-methyl)-carbamoyl]-2-methylene-hexanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-5-Methyl-3-[((S)-methylcarbamoyl-phenyl-methyl)-carbamoyl]-2-methylene-hexanoic acid

There total 4 articles about (R)-5-Methyl-3-[((S)-methylcarbamoyl-phenyl-methyl)-carbamoyl]-2-methylene-hexanoic acid 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:

(R)-2-bromo-4-methylpentanoic acid (42990-28-3) → (R)-5-Methyl-3-[((S)-methylcarbamoyl-phenyl-methyl)-carbamoyl]-2-methylene-hexanoic acid (188729-12-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 75.7 percent / H₂SO₄ / CH₂Cl₂ / 24 h / Ambient temperature

2: 49.6 percent / t-BuOK / dimethylformamide / 96 h / 0 - 5 °C

3: 61.5 percent / 95percent aq. CF₃COOH / Ambient temperature

4: 95 percent / HOBT, 4-aminopyridine, 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide / dimethylformamide / Ambient temperature

5: 1.) ammonium formate, 2.) piperidine / 1.) 10percent Pd/C

With piperidine; 4-aminopyridine; sulfuric acid; potassium tert-butylate; ammonium formate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; palladium on activated charcoal; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(97)00028-X

Reference yield:

benzyl 2<(benzyloxy)carbonyl>-3(R)-(hydroxycarbonyl)-5-methylhexanoate (155947-71-0) → (R)-5-Methyl-3-[((S)-methylcarbamoyl-phenyl-methyl)-carbamoyl]-2-methylene-hexanoic acid (188729-12-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / HOBT, 4-aminopyridine, 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide / dimethylformamide / Ambient temperature

2: 1.) ammonium formate, 2.) piperidine / 1.) 10percent Pd/C

With piperidine; 4-aminopyridine; ammonium formate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium on activated charcoal; In N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(97)00028-X

Reference yield:

2-Benzyloxycarbonyl-3R-isobutyl-succinic acid 4-tert-butyl ester 1-benzyl ester (145660-99-7) → (R)-5-Methyl-3-[((S)-methylcarbamoyl-phenyl-methyl)-carbamoyl]-2-methylene-hexanoic acid (188729-12-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 61.5 percent / 95percent aq. CF₃COOH / Ambient temperature

2: 95 percent / HOBT, 4-aminopyridine, 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide / dimethylformamide / Ambient temperature

3: 1.) ammonium formate, 2.) piperidine / 1.) 10percent Pd/C

With piperidine; 4-aminopyridine; ammonium formate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; palladium on activated charcoal; In N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(97)00028-X

upstream raw materials:

formaldehyd

2-{(R)-3-Methyl-1-[((S)-methylcarbamoyl-phenyl-methyl)-carbamoyl]-butyl}-malonic acid dibenzyl ester

(R)-2-bromo-4-methylpentanoic acid

benzyl 2<(benzyloxy)carbonyl>-3(R)-(hydroxycarbonyl)-5-methylhexanoate

Downstream raw materials:

(R)-5-Methyl-3-[((S)-methylcarbamoyl-phenyl-methyl)-carbamoyl]-2-morpholin-4-ylmethyl-hexanoic acid

(R)-5-Methyl-3-[((S)-methylcarbamoyl-phenyl-methyl)-carbamoyl]-2-phenylsulfanylmethyl-hexanoic acid

(R)-2,5-Dimethyl-3-[((S)-methylcarbamoyl-phenyl-methyl)-carbamoyl]-hexanoic acid

(2R,3R)-N⁴-Hydroxy-2-isobutyl-3-methyl-N¹-((S)-methylcarbamoyl-phenyl-methyl)-succinamide