Ethyl bromoacetate → Ethyl (1,4,8,11-tetraazacyclotetradec-1-yl)ethanoate

HRID 872941

Reaction equation

HRID 872941 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH:8]1[CH2:21][CH2:20][CH2:19][NH:18][CH2:17][CH2:16][NH:15][CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[N:8]1([CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:21][CH2:20][CH2:19][NH:18][CH2:17][CH2:16][NH:15][CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 649641,4,8,11-Tetraazacyclotetradecane

Product 1

HCID 12963737Ethyl (1,4,8,11-tetraazacyclotetradec-1-yl)ethanoate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In a first phase, ethyl (1,4,8,11-tetraazacyclotetradec-1-yl)ethanoate is obtained by slowly adding 6.68 g (40.0 mmol) of ethyl bromoacetate onto a solution of 40 g (200.0 mmol) of cyclam and 16 g (116 mmol) of potassium carbonate in 1 L of chloroform. The reaction mixture is maintained under stirring at room temperature for 48 h. After filtration on celite and evaporation of the solvent, the residue is taken up in petroleum ether. The excess cyclam is filtered off, the filtrate is concentrated and ethyl (1,4,8,11-tetraazacyclotetradec-1-yl)ethanoate (so-called compound 5.0) is thereby obtained, as 11.21 g of a slightly yellow oil (yield=98%) which is used without any purification.

Workup

  1. temperatureThe reaction mixture is maintained
  2. filtrationAfter filtration
  3. customon celite and evaporation of the solvent
  4. filtrationThe excess cyclam is filtered off
  5. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-e3de51cb07fe422a8eb5cc6ed19af054
Source dataset
uspto-grants-2015_03
Patent number
US08975395B2

Linked notes

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