1-[4-(pyridine-2-yl)-phenyl]-4(S)-hydroxy-2-N-tert-butoxycarbonylamino-5(S)-N-(N-methoxycarbonyl-(L)-tert-leucyl)amino-6-phenyl-2-azahexane

Base Information

• Chemical Name: 1-[4-(pyridine-2-yl)-phenyl]-4(S)-hydroxy-2-N-tert-butoxycarbonylamino-5(S)-N-(N-methoxycarbonyl-(L)-tert-leucyl)amino-6-phenyl-2-azahexane
• CAS No.: 198905-04-3
• Molecular Formula: C₃₅H₄₇N₅O₆
• Molecular Weight: 633.788
• Mol file: 198905-04-3.mol

Synonyms:1-[4-(pyridine-2-yl)-phenyl]-4(S)-hydroxy-2-N-tert-butoxycarbonylamino-5(S)-N-(N-methoxycarbonyl-(L)-tert-leucyl)amino-6-phenyl-2-azahexane

Chemical Property of 1-[4-(pyridine-2-yl)-phenyl]-4(S)-hydroxy-2-N-tert-butoxycarbonylamino-5(S)-N-(N-methoxycarbonyl-(L)-tert-leucyl)amino-6-phenyl-2-azahexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[4-(pyridine-2-yl)-phenyl]-4(S)-hydroxy-2-N-tert-butoxycarbonylamino-5(S)-N-(N-methoxycarbonyl-(L)-tert-leucyl)amino-6-phenyl-2-azahexane

There total 12 articles about 1-[4-(pyridine-2-yl)-phenyl]-4(S)-hydroxy-2-N-tert-butoxycarbonylamino-5(S)-N-(N-methoxycarbonyl-(L)-tert-leucyl)amino-6-phenyl-2-azahexane 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:

methyl [(2S)-3,3-dimethyl-1-({(1S)-1-[(2R)-oxiran-2-yl]-2-phenylethyl}amino)-1-oxobutan-2-yl]carbamate (1192510-20-5) + N-1-(tert-butoxycarbonyl)-N-2-[4-(pyridine-2-yl)benzyl]hydrazine (198904-85-7) → 1-[4-(pyridine-2-yl)-phenyl]-4(S)-hydroxy-2-N-tert-butoxycarbonylamino-5(S)-N-(N-methoxycarbonyl-(L)-tert-leucyl)amino-6-phenyl-2-azahexane (198905-04-3)

Guidance literature:

In water; at 60 - 65 ℃;

Reference yield:

2-bromo-pyridine (109-04-6) → 1-[4-(pyridine-2-yl)-phenyl]-4(S)-hydroxy-2-N-tert-butoxycarbonylamino-5(S)-N-(N-methoxycarbonyl-(L)-tert-leucyl)amino-6-phenyl-2-azahexane (198905-04-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) Mg, I₂, 2.) <1,3-bis(diphenylphosphino)propane>nickel(II) chloride, diisobutylaluminum hydride, 3.) aq. HCl

2: 93 percent / ethanol / 4 h / Heating

3: 89 percent / H₂ / 10percent Pd/C / methanol

4: 60 percent / propan-2-ol / 16 h / 80 °C

5: 75 percent / aq. K₂CO₃ / methanol / 3 h / Heating

6: 1.) N-ethyl-N'-<3-(dimethylamino)propyl>carbodiimide hydrochloride, 1-hydroxybenzotriazole, Et₃N / 1.) DMF, 30 min, 2.) DMF, RT, 3 h

With hydrogenchloride; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); hydrogen; iodine; diisobutylaluminium hydride; potassium carbonate; benzotriazol-1-ol; magnesium; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In methanol; ethanol; isopropyl alcohol;

DOI:10.1021/jm970873c

Reference yield:

4-(2'-pyridyl)benzaldehyde (127406-56-8) → 1-[4-(pyridine-2-yl)-phenyl]-4(S)-hydroxy-2-N-tert-butoxycarbonylamino-5(S)-N-(N-methoxycarbonyl-(L)-tert-leucyl)amino-6-phenyl-2-azahexane (198905-04-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / ethanol / 4 h / Heating

2: 89 percent / H₂ / 10percent Pd/C / methanol

3: 60 percent / propan-2-ol / 16 h / 80 °C

4: 75 percent / aq. K₂CO₃ / methanol / 3 h / Heating

5: 1.) N-ethyl-N'-<3-(dimethylamino)propyl>carbodiimide hydrochloride, 1-hydroxybenzotriazole, Et₃N / 1.) DMF, 30 min, 2.) DMF, RT, 3 h

With hydrogen; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In methanol; ethanol; isopropyl alcohol;

DOI:10.1021/jm970873c

upstream raw materials:

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

tert-butyl 2-((2S,3S)-2-hydroxy-4-phenyl-3-(amino)butyl)-2-(4-pyridin-2-ylbenzyl)hydrazinecarboxylate

2-bromo-pyridine

4-(2'-pyridyl)benzaldehyde

Downstream raw materials:

atazanavir

atazanavir sulphate

Refernces

• 1、 -. "PROCESS FOR PREPARATION OF ATAZANAVIR OR ITS BISULFATE SALT". Page/Page column 17-18. . Retrieved 2013/03/26.