Sodium Hydroxide → N1,N1'-((5-(3-(iso-Butylamino)propoxy)-1,3-phenylene)bis(methylene))-bis(N3-(3-aminopropyl)propane-1,3-diamine)

HRID 59003Notes

Reaction equation

HRID 59003 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([CH:25]=O)[CH:24]=1)[O:6][CH2:7][CH2:8][CH2:9][N:10]([CH2:18][CH:19]([CH3:21])[CH3:20])C(=O)OC(C)(C)C)=O.[NH2:27][CH2:28][CH2:29][CH2:30][NH:31][CH2:32][CH2:33][CH2:34][NH:35]C(=O)OC(C)(C)C.[BH4-].[Na+].[OH-].[Na+]>CCOC(C)=O.CO>[CH2:18]([NH:10][CH2:9][CH2:8][CH2:7][O:6][C:5]1[CH:4]=[C:3]([CH2:1][NH:35][CH2:34][CH2:33][CH2:32][NH:31][CH2:30][CH2:29][CH2:28][NH2:27])[CH:24]=[C:23]([CH2:25][NH:27][CH2:28][CH2:29][CH2:30][NH:31][CH2:32][CH2:33][CH2:34][NH2:35])[CH:22]=1)[CH:19]([CH3:20])[CH3:21]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 27866321,1-Dimethylethyl N-(3-((3-aminopropyl)amino)propyl)carbamateHCID 4311764Sodium borohydrideHCID 131737054tert-Butyl (3-(3,5-diformylphenoxy)propyl)(isobutyl)carbamate

Product 1

HCID 117718429N1,N1'-((5-(3-(iso-Butylamino)propoxy)-1,3-phenylene)bis(methylene))-bis(N3-(3-aminopropyl)propane-1,3-diamine)

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl (3-(3,5-diformylphenoxy)propyl)-(isobutyl)carbamate (0.15 g, 0.42 mmol) and MeOH (10 mL) were added to a round-bottom flask. To the solution was added tert-butyl (3-((3-aminopropyl)amino)propyl)carbamate (0.20 g, 0.84 mmol) and the reaction mixture was stirred for 24 h. Sodium borohydride (0.06 g, 1.69 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%, 50 mL) and EtOAc (50 mL) were added, the layers separated and the aqueous layer was extracted with EtOAc (50 mL). The organic layers were combined, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford the desired product as 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
  3. customto afford a white solid
  4. customthe layers 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-9b0cd479e0d445cfba4b323909771052
Source dataset
uspto-grants-2016_09
Patent number
US09439433B2

Reaction notes

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