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

Base Information

• Chemical Name: (2R,3S)-N⁴-Benzyloxy-2-isobutyl-3-methyl-N¹-((S)-methylcarbamoyl-phenyl-methyl)-succinamide
• CAS No.: 168158-38-1
• Molecular Formula: C₂₅H₃₃N₃O₄
• Molecular Weight: 439.555
• Mol file: 168158-38-1.mol

Synonyms:(2R,3S)-N⁴-Benzyloxy-2-isobutyl-3-methyl-N¹-((S)-methylcarbamoyl-phenyl-methyl)-succinamide

Chemical Property of (2R,3S)-N⁴-Benzyloxy-2-isobutyl-3-methyl-N¹-((S)-methylcarbamoyl-phenyl-methyl)-succinamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-N⁴-Benzyloxy-2-isobutyl-3-methyl-N¹-((S)-methylcarbamoyl-phenyl-methyl)-succinamide

There total 12 articles about (2R,3S)-N⁴-Benzyloxy-2-isobutyl-3-methyl-N¹-((S)-methylcarbamoyl-phenyl-methyl)-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: 57.0%

O-benzylhydoxylamine hydrochloride (2687-43-6) + (2S,3R)-2,5-Dimethyl-3-[((S)-methylcarbamoyl-phenyl-methyl)-carbamoyl]-hexanoic acid (168393-56-4) → (2R,3S)-N4-Benzyloxy-2-isobutyl-3-methyl-N1-((S)-methylcarbamoyl-phenyl-methyl)-succinamide (168158-38-1)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In dichloromethane; N,N-dimethyl-formamide; for 17h; Ambient temperature;

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

Reference yield:

(R)-2-bromo-4-methylpentanoic acid (42990-28-3) → (2R,3S)-N4-Benzyloxy-2-isobutyl-3-methyl-N1-((S)-methylcarbamoyl-phenyl-methyl)-succinamide (168158-38-1)

Guidance literature:

Multi-step reaction with 7 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

6: H₂ / 10percent Pd/C / methanol / 2 h

7: HOBT, triethylamine, 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide / dimethylformamide; CH₂Cl₂ / Ambient temperature

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

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

Reference yield:

(2R)-2-bromo-4-methylpentanoic acid t-butyl ester (130464-88-9) → (2R,3S)-N4-Benzyloxy-2-isobutyl-3-methyl-N1-((S)-methylcarbamoyl-phenyl-methyl)-succinamide (168158-38-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 49.6 percent / t-BuOK / dimethylformamide / 96 h / 0 - 5 °C

2: 61.5 percent / 95percent aq. CF₃COOH / Ambient temperature

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

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

5: H₂ / 10percent Pd/C / methanol / 2 h

6: HOBT, triethylamine, 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide / dimethylformamide; CH₂Cl₂ / Ambient temperature

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

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

upstream raw materials:

O-benzylhydoxylamine hydrochloride

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

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

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

Downstream raw materials:

KB-R₇₇₈₅