(3S,4S)-5-Cyclohexyl-3-hydroxy-4-[2-(8-propyl-6-pyridin-3-yl-[1,2,4]triazolo[4,3-a]pyrazin-3-yl)-3-pyridin-3-yl-propionylamino]-pentanoic acid [(S)-1-(3-aminomethyl-benzylcarbamoyl)-3-methyl-butyl]-amide

Base Information

• Chemical Name: (3S,4S)-5-Cyclohexyl-3-hydroxy-4-[2-(8-propyl-6-pyridin-3-yl-[1,2,4]triazolo[4,3-a]pyrazin-3-yl)-3-pyridin-3-yl-propionylamino]-pentanoic acid [(S)-1-(3-aminomethyl-benzylcarbamoyl)-3-methyl-butyl]-amide
• CAS No.: 128999-54-2
• Molecular Formula: C₄₆H₆₀N₁₀O₄
• Molecular Weight: 817.047
• Mol file: 128999-54-2.mol

Synonyms:(3S,4S)-5-Cyclohexyl-3-hydroxy-4-[2-(8-propyl-6-pyridin-3-yl-[1,2,4]triazolo[4,3-a]pyrazin-3-yl)-3-pyridin-3-yl-propionylamino]-pentanoic acid [(S)-1-(3-aminomethyl-benzylcarbamoyl)-3-methyl-butyl]-amide

Chemical Property of (3S,4S)-5-Cyclohexyl-3-hydroxy-4-[2-(8-propyl-6-pyridin-3-yl-[1,2,4]triazolo[4,3-a]pyrazin-3-yl)-3-pyridin-3-yl-propionylamino]-pentanoic acid [(S)-1-(3-aminomethyl-benzylcarbamoyl)-3-methyl-butyl]-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-5-Cyclohexyl-3-hydroxy-4-[2-(8-propyl-6-pyridin-3-yl-[1,2,4]triazolo[4,3-a]pyrazin-3-yl)-3-pyridin-3-yl-propionylamino]-pentanoic acid [(S)-1-(3-aminomethyl-benzylcarbamoyl)-3-methyl-butyl]-amide

There total 21 articles about (3S,4S)-5-Cyclohexyl-3-hydroxy-4-[2-(8-propyl-6-pyridin-3-yl-[1,2,4]triazolo[4,3-a]pyrazin-3-yl)-3-pyridin-3-yl-propionylamino]-pentanoic acid [(S)-1-(3-aminomethyl-benzylcarbamoyl)-3-methyl-butyl]-amide 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:

nicotinyl chloride (3099-31-8) → (3S,4S)-5-Cyclohexyl-3-hydroxy-4-[2-(8-propyl-6-pyridin-3-yl-[1,2,4]triazolo[4,3-a]pyrazin-3-yl)-3-pyridin-3-yl-propionylamino]-pentanoic acid [(S)-1-(3-aminomethyl-benzylcarbamoyl)-3-methyl-butyl]-amide (128999-54-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaH / 1.) DMF, 0 deg C, 2.) 2 h

2: 2 M aq. NaOH / ethanol / 1 h

3: triethylamine, 1-hydroxybenzotriazole (HOBT), ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 18 h / 20 °C

4: H₂ / 10percent Pd/C / ethanol / 1 h / 20 °C

With sodium hydroxide; hydrogen; sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00171a005

Reference yield:

{3-[((S)-2-{(3S,4S)-5-Cyclohexyl-3-hydroxy-4-[2-(8-propyl-6-pyridin-3-yl-[1,2,4]triazolo[4,3-a]pyrazin-3-yl)-3-pyridin-3-yl-propionylamino]-pentanoylamino}-4-methyl-pentanoylamino)-methyl]-benzyl}-carbamic acid benzyl ester → (3S,4S)-5-Cyclohexyl-3-hydroxy-4-[2-(8-propyl-6-pyridin-3-yl-[1,2,4]triazolo[4,3-a]pyrazin-3-yl)-3-pyridin-3-yl-propionylamino]-pentanoic acid [(S)-1-(3-aminomethyl-benzylcarbamoyl)-3-methyl-butyl]-amide (128999-54-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 20 ℃; for 1h;

DOI:10.1021/jm00171a005

Reference yield:

1,3-di(aminomethyl)benzene (1477-55-0) → (3S,4S)-5-Cyclohexyl-3-hydroxy-4-[2-(8-propyl-6-pyridin-3-yl-[1,2,4]triazolo[4,3-a]pyrazin-3-yl)-3-pyridin-3-yl-propionylamino]-pentanoic acid [(S)-1-(3-aminomethyl-benzylcarbamoyl)-3-methyl-butyl]-amide (128999-54-2)

Guidance literature:

Multi-step reaction with 7 steps

1: CH₂Cl₂ / 2 h / 0 °C

2: NaHCO₃ / acetone / 3 h / 0 °C

3: 4 M HCl / dioxane

4: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloridetriethylamine, 1-hydroxybenzotriazole hydrate / 18 h

5: 4 M HCl / dioxane

6: triethylamine, 1-hydroxybenzotriazole (HOBT), ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 18 h / 20 °C

7: H₂ / 10percent Pd/C / ethanol / 1 h / 20 °C

With hydrogenchloride; hydrogen; sodium hydrogencarbonate; benzotriazol-1-ol; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jm00171a005

upstream raw materials:

nicotinyl chloride

1,3-di(aminomethyl)benzene

3-(α-aminoacetyl)pyridine

(S)-2-(t-butoxycarbonylamino)-3-cyclohexyl-1-propanal