(S)-Methyl (3,3-dimethyl-1-oxo-1-(2-(4-(pyridin-2-yl)benzyl)hydrazinyl)butan-2-yl)carbamate

Base Information

• Chemical Name: (S)-Methyl (3,3-dimethyl-1-oxo-1-(2-(4-(pyridin-2-yl)benzyl)hydrazinyl)butan-2-yl)carbamate
• CAS No.: 857904-02-0
• Molecular Formula: C20H26N4O3
• Molecular Weight: 370.451
• ChEMBL ID: CHEMBL3526892
• DSSTox Substance ID: DTXSID601134109
• Mol file: 857904-02-0.mol

Synonyms:857904-02-0;(S)-Methyl (3,3-dimethyl-1-oxo-1-(2-(4-(pyridin-2-yl)benzyl)hydrazinyl)butan-2-yl)carbamate;Atazanavir metabolite M15;SCHEMBL3807624;CHEMBL3526892;ZQCYFRRVVVAWHJ-QGZVFWFLSA-N;DTXSID601134109;F50360;N-(Methoxycarbonyl)-3-methyl-L-valine 2-[[4-(2-pyridinyl)phenyl]methyl]hydrazide;N-[N-(Methoxycarbonyl)-L-tert-leucinyl]-N'-[4-(2-pyridyl)phenylmethyl]hydrazine;(S)-Methyl(3,3-dimethyl-1-oxo-1-(2-(4-(pyridin-2-yl)benzyl)hydrazinyl)butan-2-yl)carbamate;methyl N-[(2S)-3,3-dimethyl-1-oxo-1-[2-[(4-pyridin-2-ylphenyl)methyl]hydrazinyl]butan-2-yl]carbamate

Chemical Property of (S)-Methyl (3,3-dimethyl-1-oxo-1-(2-(4-(pyridin-2-yl)benzyl)hydrazinyl)butan-2-yl)carbamate

Chemical Property:

• XLogP3: 2.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 370.20049070
• Heavy Atom Count: 27
• Complexity: 484

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C(C(=O)NNCC1=CC=C(C=C1)C2=CC=CC=N2)NC(=O)OC
• Isomeric SMILES: CC(C)(C)[C@@H](C(=O)NNCC1=CC=C(C=C1)C2=CC=CC=N2)NC(=O)OC

Technology Process of (S)-Methyl (3,3-dimethyl-1-oxo-1-(2-(4-(pyridin-2-yl)benzyl)hydrazinyl)butan-2-yl)carbamate

There total 13 articles about (S)-Methyl (3,3-dimethyl-1-oxo-1-(2-(4-(pyridin-2-yl)benzyl)hydrazinyl)butan-2-yl)carbamate 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: 83.0%

Methyl (1S)-2,2-dimethyl-1-({(2E)-2-[4-(2-pyridinyl)benzylidene]hydrazino}carbonyl)propylcarbamate (857904-01-9) → {(S)-2,2-dimethyl-1-[N'-(4-pyridin-2-yl-benzyl)-hydrazinocarbonyl]-propyl}-carbamic acid methyl ester (857904-02-0)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In methanol; at 25 ℃; for 16h;

Reference yield: 83.0%

(S)-[2,2-dimethyl-1-(4-pyridin-2-yl-benzylidene-hydrazinocarbonyl)-propyl]-carbamic acid methyl ester (1003888-24-1) → {(S)-2,2-dimethyl-1-[N'-(4-pyridin-2-yl-benzyl)-hydrazinocarbonyl]-propyl}-carbamic acid methyl ester (857904-02-0)

Guidance literature:

With sodium formate; palladium 10% on activated carbon; In ethanol; water; at 60 ℃; for 1h;

Reference yield: 64.0%

4-(2'-pyridyl)benzaldehyde (127406-56-8) + methyl (S)-(1-hydrazinyl-3,3-dimethyl-1-oxobutan-2-yl)carbamate (198904-78-8) → {(S)-2,2-dimethyl-1-[N'-(4-pyridin-2-yl-benzyl)-hydrazinocarbonyl]-propyl}-carbamic acid methyl ester (857904-02-0)

Guidance literature:

4-(2'-pyridyl)benzaldehyde; methyl (S)-(1-hydrazinyl-3,3-dimethyl-1-oxobutan-2-yl)carbamate; With toluene-4-sulfonic acid; In tetrahydrofuran; at 20 ℃; for 1h;

With sodium cyanoborohydride; In tetrahydrofuran; at 20 ℃; Further stages.;

DOI:10.1021/jm070680h

upstream raw materials:

1-(4-(pyridin-2-yl)benzyl)hydrazine

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

(S)-[2,2-dimethyl-1-(4-pyridin-2-yl-benzylidene-hydrazinocarbonyl)-propyl]-carbamic acid methyl ester

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

Downstream raw materials:

{(1S,2S)-1-benzyl-2-hydroxy-3-[N'-((S)-2-methoxycarbonylamino-3,3-dimethyl-butyryl)-N-(4-pyridin-2-yl-benzyl)-hydrazino]-propyl}-carbamic acid tert-butyl ester

{(S)-1-[N'-((2S,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-N'-(4-pyridin-2-yl-benzyl)-hydrazinocarbonyl]-2,2-dimethyl-propyl}-carbamic acid methyl ester

atazanavir

methyl (1R,3S)-3-((2S,3S)-3-hydroxy-4-(2-((S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoyl)-1-(4-(pyridin-2-yl)benzyl)hydrazinyl)-1-phenylbutan-2-ylcarbamoyl)-2,2-dimethylcyclobutylcarbamate