N-(4-cyanobutyl)-3-<<5-<(benzyloxy)-tert-butoxy-carbonylamino>pentyl>carbamoyl>-O-benzylpropionohydroxamic acid

Base Information

• Chemical Name: N-(4-cyanobutyl)-3-<<5-<(benzyloxy)-tert-butoxy-carbonylamino>pentyl>carbamoyl>-O-benzylpropionohydroxamic acid
• CAS No.: 129245-22-3
• Molecular Formula: C₃₃H₄₆N₄O₆
• Molecular Weight: 594.751
• Mol file: 129245-22-3.mol

Synonyms:N-(4-cyanobutyl)-3-<<5-<(benzyloxy)-tert-butoxy-carbonylamino>pentyl>carbamoyl>-O-benzylpropionohydroxamic acid

Chemical Property of N-(4-cyanobutyl)-3-<<5-<(benzyloxy)-tert-butoxy-carbonylamino>pentyl>carbamoyl>-O-benzylpropionohydroxamic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(4-cyanobutyl)-3-<<5-<(benzyloxy)-tert-butoxy-carbonylamino>pentyl>carbamoyl>-O-benzylpropionohydroxamic acid

There total 6 articles about N-(4-cyanobutyl)-3-<<5-<(benzyloxy)-tert-butoxy-carbonylamino>pentyl>carbamoyl>-O-benzylpropionohydroxamic acid 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: 99.0%

O-benzyl-N-(5-aminopentyl)-N-(tert-butoxycarbonyl)hydroxylamine (129245-21-2) + N-(4-Cyanobutyl)-N-(benzyloxy)succinamic Acid (112139-60-3) → N-(4-cyanobutyl)-3-<<5-<(benzyloxy)-tert-butoxy-carbonylamino>pentyl>carbamoyl>-O-benzylpropionohydroxamic acid (129245-22-3)

Guidance literature:

With diphenyl phosphoryl azide; triethylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 17h;

DOI:10.1021/jm00115a006

Reference yield:

δ-chlorovaleronitrile (6280-87-1) → N-(4-cyanobutyl)-3-<<5-<(benzyloxy)-tert-butoxy-carbonylamino>pentyl>carbamoyl>-O-benzylpropionohydroxamic acid (129245-22-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) sodium iodide, 80percent sodium hydride / 1.) DMF, 15 min, 2.) DMF, 80 - 85 deg C, 4 h

2: 83 percent / conc. NH₄OH, NH₃ / Raney nickel / methanol / 3.5 h / 0 °C / 2844.3 - 2999.5 Torr

3: 65 percent / 4-dimethylaminopyridine, 1,3-dicyclohexylcarbodiimide / CH₂Cl₂ / 1.) 0 deg C, 45 min, 2.) room temp., 19 h

With dmap; ammonium hydroxide; sodium hydride; dicyclohexyl-carbodiimide; sodium iodide; nickel; In methanol; dichloromethane;

DOI:10.1016/S0040-4020(01)81074-7

Reference yield:

tert-butyl N-(benzyloxy)carbamate (79722-21-7) → N-(4-cyanobutyl)-3-<<5-<(benzyloxy)-tert-butoxy-carbonylamino>pentyl>carbamoyl>-O-benzylpropionohydroxamic acid (129245-22-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) sodium iodide, 80percent sodium hydride / 1.) DMF, 15 min, 2.) DMF, 80 - 85 deg C, 4 h

2: 83 percent / conc. NH₄OH, NH₃ / Raney nickel / methanol / 3.5 h / 0 °C / 2844.3 - 2999.5 Torr

3: 65 percent / 4-dimethylaminopyridine, 1,3-dicyclohexylcarbodiimide / CH₂Cl₂ / 1.) 0 deg C, 45 min, 2.) room temp., 19 h

With dmap; ammonium hydroxide; sodium hydride; dicyclohexyl-carbodiimide; sodium iodide; nickel; In methanol; dichloromethane;

DOI:10.1016/S0040-4020(01)81074-7

upstream raw materials:

O-benzyl-N-(5-aminopentyl)-N-(tert-butoxycarbonyl)hydroxylamine

N-(4-Cyanobutyl)-N-(benzyloxy)succinamic Acid

δ-chlorovaleronitrile

tert-butyl N-(benzyloxy)carbamate

Downstream raw materials:

22-(tert-butoxycarbonyl)-11,22-bis(benzyloxy)-12,15-dioxo-11,16,22-triaza-2,5,8-trioxadocosane

N-(4-cyanobutyl)-3-<<5-<(benzyloxy)amino>pentyl>carbamoyl>-O-benzylpropionohydroxamic acid

N'-<5-<<4-<<5-pentyl>amino>-1,4-dioxobutyl>(phenylmethoxy)amino>pentyl>-N-(4-cyanobutyl)-N-(phenylmethoxy)butanediamide

27--6,17-bis(benzyloxy)-7,10,18,21-tetraoxo-6,11,17,22-tetraazaheptacosanenitrile