Des-N-(methoxycarbonyl)-L-tert-leucine Bis-Boc Atazanavir

Base Information

• Chemical Name: Des-N-(methoxycarbonyl)-L-tert-leucine Bis-Boc Atazanavir
• CAS No.: 198904-86-8
• Molecular Formula: C32H42N4O5
• Molecular Weight: 562.709
• European Community (EC) Number: 606-396-7
• UNII: ZD25TA7YUL
• DSSTox Substance ID: DTXSID40477277
• Nikkaji Number: J978.835B
• Mol file: 198904-86-8.mol

Synonyms:198904-86-8;Des-N-(methoxycarbonyl)-L-tert-leucine Bis-Boc Atazanavir;ZD25TA7YUL;tert-Butyl 2-((2S,3S)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-4-phenylbutyl)-2-(4-(pyridin-2-yl)benzyl)hydrazinecarboxylate;tert-butyl N-[[(2S,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylbutyl]-[(4-pyridin-2-ylphenyl)methyl]amino]carbamate;2-[(2S,3S)-3-[[(1,1-Dimethylethoxy)carbonyl]amino]-2-hydroxy-4-phenylbutyl] -2-[[4-(2-pyridinyl)phenyl]methyl]hydrazinecarboxylic Acid 1,1-Dimethylethyl Ester;Hydrazinecarboxylic acid, 2-((2S,3S)-3-(((1,1-dimethylethoxy)carbonyl)amino)-2-hydroxy-4-phenylbutyl)-2-((4-(2-pyridinyl)phenyl)methyl)-, 1,1-dimethylethyl ester;tert-Butyl N-[(1S,2S)-1-Benzyl-3-[(tert-butoxycarbonylamino)-[[4-(2-pyridyl)phenyl]methyl]amino]-2-hydroxy-propyl]carbamate;Hydrazinecarboxylic acid, 2-[(2S,3S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-hydroxy-4-phenylbutyl]-2-[[4-(2-pyridinyl)phenyl]methyl]-, 1,1-dimethylethyl ester;UNII-ZD25TA7YUL;SCHEMBL2175950;DTXSID40477277;BCP12785;AKOS015950829;1-[4-(Pyridin-2-yl)phenyl]-5(S)-2,5-bis[(tert-butyloxycarbonyl)-amino]-4(S)-hydroxyl-6-phenyl-2-azahexane;AC-27024;A855354;A1-03405;ATAZANAVIR SULFATE IMPURITY J [EP IMPURITY];1-(4-(pyridin-2-yl)phenyl)-5(s)-2,5-bis ((tert-butyloxycarbonyl)amino)-4(s)-hydroxyl-6-phenyl-2-azahexane;2-[(2S,3S)-3-[[(1,1-Dimethylethoxy)carbonyl]amino]-2-hydroxy-4-phenylbutyl]-2-[[4-(2-pyridinyl)phenyl]methyl]hydrazinecarboxylic acid tert-butyl ester;tert-Butyl 2-((2S,3S)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-4-phenylbutyl)-2-(4-(pyridin-2-yl)benzyl)hydrazinecarboxylate.;TERT-BUTYL 2-((2S,3S)-3-(TERT-BUTOXYFORMAMIDO)-2-HYDROXY-4-PHENYLBUTYL)-2-((4-(PYRIDIN-2-YL)PHENYL)METHYL)HYDRAZINE-1-CARBOXYLATE;tert-Butyl 2-{(2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-4-phenylbutyl}-2-{[4-(pyridin-2-yl)phenyl]methyl}hydrazine-1-carboxylate;tert-Butyl2-((2S,3S)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-4-phenylbutyl)-2-(4-(pyridin-2-yl)benzyl)hydrazinecarboxylate

Chemical Property of Des-N-(methoxycarbonyl)-L-tert-leucine Bis-Boc Atazanavir

Chemical Property:

• Appearance/Colour: off-white
• Vapor Pressure: 0-0Pa at 25℃
• Melting Point: 184 °C
• Refractive Index: 1.567
• PKA: 10.05±0.50(Predicted)
• PSA: 113.02000
• Density: 1.157 g/cm³
• LogP: 6.26900
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 14
• Exact Mass: 562.31552045
• Heavy Atom Count: 41
• Complexity: 797

Purity/Quality:

99% ^*data from raw suppliers

Des-N-(methoxycarbonyl)-L-tert-leucineBis-BocAtazanavir ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=CC=C1)C(CN(CC2=CC=C(C=C2)C3=CC=CC=N3)NC(=O)OC(C)(C)C)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CC=CC=C1)[C@H](CN(CC2=CC=C(C=C2)C3=CC=CC=N3)NC(=O)OC(C)(C)C)O
• Uses: An intermediate for the synthesis of Atazanavir and the preparation of some peptide analogs Des-N-(methoxycarbonyl)-L-tert-leucine Bis-Boc Atazanavir is an intermediate for the synthesis of Atazanavir (A790051) and the preparation of some peptide analogs.

Technology Process of Des-N-(methoxycarbonyl)-L-tert-leucine Bis-Boc Atazanavir

There total 19 articles about Des-N-(methoxycarbonyl)-L-tert-leucine Bis-Boc Atazanavir 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: 85.4%

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8) + N-1-(tert-butoxycarbonyl)-N-2-[4-(pyridine-2-yl)benzyl]hydrazine (198904-85-7) → 1-[4-(pyridine-2-yl)phenyl]-5(S)-2,5-bis[(tert-butyloxycarbonyl)amino]-4(S)-hydroxy-6-phenyl-2-azahexane (198904-86-8)

Guidance literature:

In isopropyl alcohol; for 24h; Inert atmosphere; Reflux; Large scale;

DOI:10.1021/op025504r

Reference yield: 60.0%

1-(4-(pyridin-2-yl)-phenyl)-1-oxo-5(S)-2,5-di[(tert-butoxycarbonyl)amino]-4(S)-hydroxy-6-phenyl-2-azahexane (198905-10-1) → 1-[4-(pyridine-2-yl)phenyl]-5(S)-2,5-bis[(tert-butyloxycarbonyl)amino]-4(S)-hydroxy-6-phenyl-2-azahexane (198904-86-8)

Guidance literature:

With diisobutylaluminium hydride; at 0 ℃; for 2.5h;

DOI:10.1016/S0040-4039(98)00897-1

Reference yield: 57.0%

(1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester (98760-08-8,98818-34-9,98818-35-0,103127-56-6,98737-29-2) + N-1-(tert-butoxycarbonyl)-N-2-[4-(pyridine-2-yl)benzyl]hydrazine (198904-85-7) → 1-[4-(pyridine-2-yl)phenyl]-5(S)-2,5-bis[(tert-butyloxycarbonyl)amino]-4(S)-hydroxy-6-phenyl-2-azahexane (198904-86-8)

Guidance literature:

In isopropyl alcohol; at 65 ℃; for 16h;

upstream raw materials:

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

N-1-(tert-butoxycarbonyl)-N-2-[4-(pyridine-2-yl)benzyl]hydrazine

1-(4-(pyridin-2-yl)-phenyl)-1-oxo-5(S)-2,5-di[(tert-butoxycarbonyl)amino]-4(S)-hydroxy-6-phenyl-2-azahexane

2-bromo-pyridine

Downstream raw materials:

atazanavir sulphate

(2S,3S)-3-amino-4-phenyl-1-(1-(4-(pyridin-2-yl)benzyl)hydrazinyl)butan-2-ol hydrochloride

1-[4-(pyridine-2-yl)phenyl]-(5S)-2,5-diamino-(4S)-hydroxy-6-phenyl-2-azahexane

1-[4-(pyridin-2-yl)-phenyl]-4(S)-hydroxy-5(S)-2,5-diamino-6-phenyl-2-azahexane hydrochloride

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF ATAZANAVIR SULFATE SUBSTANTIALLY FREE OF DIASTEREOMERS". Page/Page column 16. . Retrieved 2011/10/03.
• 2、 -. "Azapeptide derivatives as HIV protease inhibitors". Page/Page column 33-34. . Retrieved 2009/01/24.