Tetraethylenepentamine → 3-(4-Nitrobenzyl)-2,6-dioxo-1,4,7,10,13,16-hexaazacyclooctadecane

HRID 719664Notes

Reaction equation

HRID 719664 reaction equation
[Na].[NH2:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][NH:8][CH2:9][CH2:10][NH:11][CH2:12][CH2:13][NH2:14].CO[C:17](=[O:35])[C@H:18]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=1)[NH:19][CH2:20][C:21]([O:23]C)=O>CO>[N+:32]([C:29]1[CH:28]=[CH:27][C:26]([CH2:25][CH:18]2[NH:19][CH2:20][C:21](=[O:23])[NH:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][NH:8][CH2:9][CH2:10][NH:11][CH2:12][CH2:13][NH:14][C:17]2=[O:35])=[CH:31][CH:30]=1)([O-:34])=[O:33]

Participants

5

Reactant 3

HCID 8197TetraethylenepentamineHCID 5360545SodiumHCID 68574020N-((Methoxycarbonyl)methyl)4-Nitrophenylalanine Methyl Ester

Product 1

HCID 158906023-(4-Nitrobenzyl)-2,6-dioxo-1,4,7,10,13,16-hexaazacyclooctadecaneYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium (20 mmol) was dissolved in dry methanol (100 ml) at room temperature under nitrogen atmosphere and to this solution was added tetraethylenepentamine (18 mmol) and N-((Methoxycarbonyl)methyl)-4-Nitrophenylaianine methyl ester (3) (18 mmol). This solution was refluxed for 72 hours after which the solvent was removed and the residue was purified on silica gel chromatography with chloroformelmethanol/NH3 (aq) (75:20:5), affording a yellow powder. The yield was 50%.

Workup

  1. temperatureThis solution was refluxed for 72 hours after which the solvent
  2. customwas removed
  3. customthe residue was purified on silica gel chromatography with chloroformelmethanol/NH3 (aq) (75:20:5)
  4. customaffording a yellow powder

Sources & evidence

ORD record
ord-96496973510048c489a04932f62cb52b
Source dataset
uspto-grants-2006_11
Patent number
US07132513B2

Reaction notes

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