N⁽¹⁾-p-nitrobenzoyl-N⁽⁴⁾,N⁽⁹⁾,N⁽¹²⁾-tri-(tert-butyloxycarbonyl)-1,12-diamino-4,9-diazadodecane

Base Information

• Chemical Name: N⁽¹⁾-p-nitrobenzoyl-N⁽⁴⁾,N⁽⁹⁾,N⁽¹²⁾-tri-(tert-butyloxycarbonyl)-1,12-diamino-4,9-diazadodecane
• CAS No.: 1297523-34-2
• Molecular Formula: C₃₂H₅₃N₅O₉
• Molecular Weight: 651.801

Synonyms:N⁽¹⁾-p-nitrobenzoyl-N⁽⁴⁾,N⁽⁹⁾,N⁽¹²⁾-tri-(tert-butyloxycarbonyl)-1,12-diamino-4,9-diazadodecane

Chemical Property of N⁽¹⁾-p-nitrobenzoyl-N⁽⁴⁾,N⁽⁹⁾,N⁽¹²⁾-tri-(tert-butyloxycarbonyl)-1,12-diamino-4,9-diazadodecane

Chemical Property:

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Technology Process of N⁽¹⁾-p-nitrobenzoyl-N⁽⁴⁾,N⁽⁹⁾,N⁽¹²⁾-tri-(tert-butyloxycarbonyl)-1,12-diamino-4,9-diazadodecane

There total 7 articles about N⁽¹⁾-p-nitrobenzoyl-N⁽⁴⁾,N⁽⁹⁾,N⁽¹²⁾-tri-(tert-butyloxycarbonyl)-1,12-diamino-4,9-diazadodecane 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: 87.0%

tri-Boc-spermine (114459-62-0) + 4-nitro-benzoyl chloride (122-04-3) → N(1)-p-nitrobenzoyl-N(4),N(9),N(12)-tri-(tert-butyloxycarbonyl)-1,12-diamino-4,9-diazadodecane (1297523-34-2)

Guidance literature:

With triethylamine; In toluene; at 60 ℃; for 8h;

DOI:10.1039/c0jm04064a

Reference yield:

3-(4-[(2-cyanoethyl)amino]butylamino)propanenitrile (14209-32-6) → N(1)-p-nitrobenzoyl-N(4),N(9),N(12)-tri-(tert-butyloxycarbonyl)-1,12-diamino-4,9-diazadodecane (1297523-34-2)

Guidance literature:

Multi-step reaction with 6 steps

1: triethylamine / methanol / 24 h / 0 - 20 °C

2: palladium on activated charcoal; lithium hydroxide monohydrate; hydrogen / 1,4-dioxane; water / 20 °C

3: methanol / -78 - 0 °C / Inert atmosphere

4: methanol / 16 h / 0 - 20 °C / Inert atmosphere

5: water; potassium carbonate / 3 h / Reflux

6: triethylamine / toluene / 8 h / 60 °C

With lithium hydroxide monohydrate; palladium on activated charcoal; water; hydrogen; potassium carbonate; triethylamine; In 1,4-dioxane; methanol; water; toluene;

DOI:10.1039/c0jm04064a

Reference yield:

1-trifluoroacetyl-5,10,14-tris-Boc-spermine (201984-66-9) → N(1)-p-nitrobenzoyl-N(4),N(9),N(12)-tri-(tert-butyloxycarbonyl)-1,12-diamino-4,9-diazadodecane (1297523-34-2)

Guidance literature:

Multi-step reaction with 2 steps

1: water; potassium carbonate / 3 h / Reflux

2: triethylamine / toluene / 8 h / 60 °C

With water; potassium carbonate; triethylamine; In toluene;

DOI:10.1039/c0jm04064a

upstream raw materials:

3-(4-[(2-cyanoethyl)amino]butylamino)propanenitrile

tri-Boc-spermine

4-nitro-benzoyl chloride

di-tert-butyl butane-1,4-diylbis((3-aminopropyl)carbamate)

Downstream raw materials:

N⁽¹⁾-(p-aminobenzoyl)-N⁽⁴⁾,N⁽⁹⁾,N⁽¹²⁾-tri-(tert-butyloxycarbonyl)-1,12-diamino-4,9-diazadodecane

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