L-Alaninamide, N-[(1,1-dimethylethoxy)carbonyl]-L-tyrosyl-L-prolyl-L-phenylalanyl-L-prolyl- 3-[(3-nitro-2-pyridinyl)dithio]-

Base Information

• Chemical Name: L-Alaninamide, N-[(1,1-dimethylethoxy)carbonyl]-L-tyrosyl-L-prolyl-L-phenylalanyl-L-prolyl- 3-[(3-nitro-2-pyridinyl)dithio]-
• CAS No.: 185141-52-0
• Molecular Formula: C₄₁H₅₀N₈O₁₀S₂
• Molecular Weight: 879.028
• Mol file: 185141-52-0.mol

Synonyms:

Chemical Property of L-Alaninamide, N-[(1,1-dimethylethoxy)carbonyl]-L-tyrosyl-L-prolyl-L-phenylalanyl-L-prolyl- 3-[(3-nitro-2-pyridinyl)dithio]-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-Alaninamide, N-[(1,1-dimethylethoxy)carbonyl]-L-tyrosyl-L-prolyl-L-phenylalanyl-L-prolyl- 3-[(3-nitro-2-pyridinyl)dithio]-

There total 6 articles about L-Alaninamide, N-[(1,1-dimethylethoxy)carbonyl]-L-tyrosyl-L-prolyl-L-phenylalanyl-L-prolyl- 3-[(3-nitro-2-pyridinyl)dithio]- 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: 52.0%

3-nitro-2-pyridinesulfenyl chloride (68206-45-1) + [(S)-2-[(S)-2-((S)-1-Benzyl-2-{(S)-2-[(R)-1-carbamoyl-2-(4-methoxy-benzylsulfanyl)-ethylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethylcarbamoyl)-pyrrolidin-1-yl]-1-(4-hydroxy-benzyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester (185141-49-5) → [(S)-2-[(S)-2-((S)-1-Benzyl-2-{(S)-2-[(R)-1-carbamoyl-2-(3-nitro-pyridin-2-yldisulfanyl)-ethylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethylcarbamoyl)-pyrrolidin-1-yl]-1-(4-hydroxy-benzyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester (185141-52-0)

Guidance literature:

In dichloromethane; at 0 ℃;

DOI:10.1246/bcsj.69.3607

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → [(S)-2-[(S)-2-((S)-1-Benzyl-2-{(S)-2-[(R)-1-carbamoyl-2-(3-nitro-pyridin-2-yldisulfanyl)-ethylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethylcarbamoyl)-pyrrolidin-1-yl]-1-(4-hydroxy-benzyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester (185141-52-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 86 percent / Et₃N, HOBt, EDC*HCl / dimethylformamide / 1.) 0 deg C, 2 h, 2.) room temperature, overnight

2: 98 percent / 1 M NaOH / methanol / 2 h / Ambient temperature

3: 82 percent / Et₃N, HOBt, EDC*HCl / dimethylformamide / 1.) 0 deg C, 2 h, 2.) room temperature, overnight

4: 96 percent / 4.5 M HCl / dioxane / 1 h / 0 °C

5: 81 percent / Et₃N, HOBt, EDC*HCl / dimethylformamide / 1.) 0 deg C, 2 h, 2.) room temperature, overnight

6: 52 percent / CH₂Cl₂ / 0 °C

With hydrogenchloride; sodium hydroxide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.69.3607

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanyl-L-proline (23420-32-8) → [(S)-2-[(S)-2-((S)-1-Benzyl-2-{(S)-2-[(R)-1-carbamoyl-2-(3-nitro-pyridin-2-yldisulfanyl)-ethylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethylcarbamoyl)-pyrrolidin-1-yl]-1-(4-hydroxy-benzyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester (185141-52-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / Et₃N, HOBt, EDC*HCl / dimethylformamide / 1.) 0 deg C, 2 h, 2.) room temperature, overnight

2: 96 percent / 4.5 M HCl / dioxane / 1 h / 0 °C

3: 81 percent / Et₃N, HOBt, EDC*HCl / dimethylformamide / 1.) 0 deg C, 2 h, 2.) room temperature, overnight

4: 52 percent / CH₂Cl₂ / 0 °C

With hydrogenchloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.69.3607

upstream raw materials:

3-nitro-2-pyridinesulfenyl chloride

[(S)-2-[(S)-2-((S)-1-Benzyl-2-{(S)-2-[(R)-1-carbamoyl-2-(4-methoxy-benzylsulfanyl)-ethylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethylcarbamoyl)-pyrrolidin-1-yl]-1-(4-hydroxy-benzyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

N-tert-butoxycarbonyl-L-phenylalanine

N-tert-butoxycarbonyl-L-phenylalanyl-L-proline