(2R,3R)-N⁴-Benzyloxy-2-isobutyl-N¹-((S)-methylcarbamoyl-phenyl-methyl)-3-morpholin-4-ylmethyl-succinamide

Base Information

• Chemical Name: (2R,3R)-N⁴-Benzyloxy-2-isobutyl-N¹-((S)-methylcarbamoyl-phenyl-methyl)-3-morpholin-4-ylmethyl-succinamide
• CAS No.: 168158-24-5
• Molecular Formula: C₂₉H₄₀N₄O₅
• Molecular Weight: 524.66

Synonyms:(2R,3R)-N⁴-Benzyloxy-2-isobutyl-N¹-((S)-methylcarbamoyl-phenyl-methyl)-3-morpholin-4-ylmethyl-succinamide

Chemical Property of (2R,3R)-N⁴-Benzyloxy-2-isobutyl-N¹-((S)-methylcarbamoyl-phenyl-methyl)-3-morpholin-4-ylmethyl-succinamide

Chemical Property:

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Technology Process of (2R,3R)-N⁴-Benzyloxy-2-isobutyl-N¹-((S)-methylcarbamoyl-phenyl-methyl)-3-morpholin-4-ylmethyl-succinamide

There total 7 articles about (2R,3R)-N⁴-Benzyloxy-2-isobutyl-N¹-((S)-methylcarbamoyl-phenyl-methyl)-3-morpholin-4-ylmethyl-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: 51.0%

O-benzylhydoxylamine hydrochloride (2687-43-6) + (R)-5-Methyl-3-[((S)-methylcarbamoyl-phenyl-methyl)-carbamoyl]-2-morpholin-4-ylmethyl-hexanoic acid (190909-08-1) → (2R,3R)-N4-Benzyloxy-2-isobutyl-N1-((S)-methylcarbamoyl-phenyl-methyl)-3-morpholin-4-ylmethyl-succinamide (168158-24-5)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; N,N-dimethyl-formamide; Ambient temperature;

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

Reference yield:

(R)-2-bromo-4-methylpentanoic acid (42990-28-3) → (2R,3R)-N4-Benzyloxy-2-isobutyl-N1-((S)-methylcarbamoyl-phenyl-methyl)-3-morpholin-4-ylmethyl-succinamide (168158-24-5)

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: 70 percent / 48 h / 40 - 45 °C

7: 51 percent / HOBT, 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide, N-methylmorpholine / dimethylformamide; CH₂Cl₂ / Ambient temperature

With piperidine; 4-methyl-morpholine; 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:

(2R)-2-bromo-4-methylpentanoic acid t-butyl ester (130464-88-9) → (2R,3R)-N4-Benzyloxy-2-isobutyl-N1-((S)-methylcarbamoyl-phenyl-methyl)-3-morpholin-4-ylmethyl-succinamide (168158-24-5)

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: 70 percent / 48 h / 40 - 45 °C

6: 51 percent / HOBT, 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide, N-methylmorpholine / dimethylformamide; CH₂Cl₂ / Ambient temperature

With piperidine; 4-methyl-morpholine; 4-aminopyridine; 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

upstream raw materials:

O-benzylhydoxylamine hydrochloride

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

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

(2R)-2-bromo-4-methylpentanoic acid t-butyl ester

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