1,1-Dimethylethyl N-(3-((3-aminopropyl)amino)propyl)carbamate → Di-tert-butyl ((((((5-butoxy-1,3-phenylene)bis(methylene))bis(azanediyl))-bis(propane-3,1-diyl))bis(azanediyl))bis(propane-3,1-diyl))dicarbamate

HRID 58978Notes

Reaction equation

HRID 58978 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH:14]=O)[CH:9]=[C:10]([CH:13]=1)[CH:11]=O)[CH2:2][CH2:3][CH3:4].[NH2:16][CH2:17][CH2:18][CH2:19][NH:20][CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28].[BH4-].[Na+]>CO>[CH2:1]([O:5][C:6]1[CH:13]=[C:10]([CH2:11][NH:16][CH2:17][CH2:18][CH2:19][NH:20][CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:28])[CH3:30])[CH:9]=[C:8]([CH2:14][NH:16][CH2:17][CH2:18][CH2:19][NH:20][CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:28])([CH3:30])[CH3:29])[CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 27866321,1-Dimethylethyl N-(3-((3-aminopropyl)amino)propyl)carbamateHCID 4311764Sodium borohydrideHCID 117704501HCID 117704501, compound

Product 1

HCID 131737045Di-tert-butyl ((((((5-butoxy-1,3-phenylene)bis(methylene))bis(azanediyl))-bis(propane-3,1-diyl))bis(azanediyl))bis(propane-3,1-diyl))dicarbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Butoxyisophthalaldehyde (0.80 g, 0.85 mmol) and MeOH (15 mL) were added to a round-bottom flask. To the solution was added tert-butyl (3-((3-aminopropyl)amino)propyl)-carbamate (0.39 g, 1.70 mmol), and the reaction mixture was stirred at rt for 24 h. Sodium borohydride (0.13 g, 3.40 mmol) was added and the reaction mixture stirred for 1 h. The reaction mixture was concentrated under reduced pressure and aq. NaOH (10%, 50 mL) and EtOAc (50 mL) were added. The layers were separated and the aqueous layer was extracted with EtOAc (50 mL). The organic layers combined, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford the desired product as a clear oil which was used without further purification.

Workup

  1. stirringthe reaction mixture stirred for 1 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure and aq. NaOH (10%, 50 mL) and EtOAc (50 mL)
  3. additionwere added
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with EtOAc (50 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9d17d4f717474493a20f6ff9a4d91f4a
Source dataset
uspto-grants-2016_09
Patent number
US09439433B2

Reaction notes

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