Alaninamide, 3-(4-chloro-3-pyridinyl)-N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl-L-prolyl -2-methyl-N-[(1S)-1-phenylethyl]-

Base Information

• Chemical Name: Alaninamide, 3-(4-chloro-3-pyridinyl)-N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl-L-prolyl -2-methyl-N-[(1S)-1-phenylethyl]-
• CAS No.: 656801-24-0
• Molecular Formula: C30H40ClN5O5
• Molecular Weight: 586.131
• Mol file: 656801-24-0.mol

Synonyms:

Chemical Property of Alaninamide, 3-(4-chloro-3-pyridinyl)-N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl-L-prolyl -2-methyl-N-[(1S)-1-phenylethyl]-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Alaninamide, 3-(4-chloro-3-pyridinyl)-N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl-L-prolyl -2-methyl-N-[(1S)-1-phenylethyl]-

There total 5 articles about Alaninamide, 3-(4-chloro-3-pyridinyl)-N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl-L-prolyl -2-methyl-N-[(1S)-1-phenylethyl]- 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%

(2S)-(N-tert-butoxycarbonylamino)-3-(4'-chloropyridin-3'-yl)propionic acid (656801-23-9) + (S)-Pyrrolidine-2-carboxylic acid [1-methyl-1-((S)-1-phenyl-ethylcarbamoyl)-ethyl]-amide → ((S)-1-(4-Chloro-pyridin-3-ylmethyl)-2-{(S)-2-[1-methyl-1-((S)-1-phenyl-ethylcarbamoyl)-ethylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethyl)-carbamic acid tert-butyl ester (656801-24-0)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at -23 - 20 ℃; for 17h;

DOI:10.1039/b308750f

Reference yield:

4-chloro-3-iodopyridine (89167-34-0) → ((S)-1-(4-Chloro-pyridin-3-ylmethyl)-2-{(S)-2-[1-methyl-1-((S)-1-phenyl-ethylcarbamoyl)-ethylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethyl)-carbamic acid tert-butyl ester (656801-24-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Zn / dimethylformamide / 1.58 h

1.2: 36 percent / Pd(PPh₃)2Cl₂ / dimethylformamide / 20 °C

2.1: 58 percent / aq. LiOH / tetrahydrofuran / 20 °C

3.1: 52 percent / HOBt; N-methylmorpholine; EDCl / dimethylformamide / 17 h / -23 - 20 °C

With 4-methyl-morpholine; lithium hydroxide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; zinc; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1039/b308750f

Reference yield:

4-chlorpyridine hydrochloride (7379-35-3) → ((S)-1-(4-Chloro-pyridin-3-ylmethyl)-2-{(S)-2-[1-methyl-1-((S)-1-phenyl-ethylcarbamoyl)-ethylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethyl)-carbamic acid tert-butyl ester (656801-24-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: LDA / tetrahydrofuran; hexane / -78 °C

1.2: 61 percent / I₂ / tetrahydrofuran; hexane / 4 h / -65 - 20 °C

2.1: Zn / dimethylformamide / 1.58 h

2.2: 36 percent / Pd(PPh₃)2Cl₂ / dimethylformamide / 20 °C

3.1: 58 percent / aq. LiOH / tetrahydrofuran / 20 °C

4.1: 52 percent / HOBt; N-methylmorpholine; EDCl / dimethylformamide / 17 h / -23 - 20 °C

With 4-methyl-morpholine; lithium hydroxide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; zinc; lithium diisopropyl amide; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

DOI:10.1039/b308750f

upstream raw materials:

(2S)-(N-tert-butoxycarbonylamino)-3-(4'-chloropyridin-3'-yl)propionic acid

4-chloro-3-iodopyridine

4-chlorpyridine hydrochloride

N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester