Sodium Hydroxide → Di-tert-butyl ((((([1,1'-biphenyl]-3,5-diylbis(methylene))bis(azanediyl))-bis(propane-3,1-diyl))bis(azanediyl))bis(propane-3,1-diyl))dicarbamate

HRID 58984Notes

Reaction equation

HRID 58984 reaction equation
[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[C:5]([CH:7]=O)[CH:4]=[C:3]([CH:9]=O)[CH:2]=1.[NH2:17][CH2:18][CH2:19][CH2:20][NH:21][CH2:22][CH2:23][CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29].[BH4-].[Na+].[OH-:35].[Na+]>CCOC(C)=O.CO>[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[C:5]([CH2:7][NH:17][CH2:18][CH2:19][CH2:20][NH:21][CH2:22][CH2:23][CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:29])([CH3:31])[CH3:30])[CH:4]=[C:3]([CH2:9][NH:17][CH2:18][CH2:19][CH2:20][NH:21][CH2:22][CH2:23][CH2:24][NH:25][C:26](=[O:27])[O:35][C:28]([CH3:30])([CH3:29])[CH3:31])[CH:2]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 27866321,1-Dimethylethyl N-(3-((3-aminopropyl)amino)propyl)carbamateHCID 4311764Sodium borohydrideHCID 14199327[1,1'-Biphenyl]-3,5-dicarboxaldehyde

Product 1

HCID 131737041Di-tert-butyl ((((([1,1'-biphenyl]-3,5-diylbis(methylene))bis(azanediyl))-bis(propane-3,1-diyl))bis(azanediyl))bis(propane-3,1-diyl))dicarbamate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

[1,1′-Biphenyl]-3,5-dicarbaldehyde (3.62 g, 17.2 mmol, 1) and MeOH (100 mL) were added to a round-bottom flask. To the solution was added tert-butyl (3-((3-aminopropyl)amino)propyl)-carbamate (7.96 g, 34.4 mmol), and the reaction mixture was stirred at rt for 24 h. Sodium borohydride (2.62 g, 69.0 mmol) was added and the reaction mixture stirred for 1 h. The reaction mixture was concentrated under reduced pressure to afford a white solid. Aqueous NaOH (10%, 200 mL) and EtOAc (200 mL) were added, and the reaction mixture was stirred for 1 h. The layers were separated, and the aqueous layer was extracted with EtOAc (200 mL). The organic layers were combined, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford a clear oil that was used without further purification.

Workup

  1. stirringthe reaction mixture stirred for 1 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto afford a white solid
  4. stirringthe reaction mixture was stirred for 1 h
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with EtOAc (200 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto afford a clear oil that
  11. customwas used without further purification

Sources & evidence

ORD record
ord-69d1c8fb96f64d3299422fbdc5a76e3b
Source dataset
uspto-grants-2016_09
Patent number
US09439433B2

Reaction notes

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