Hydrogen Bromide → N4, N7, N10-Triscarboxymethyl-1,13-bisbenzyloxy-5,9-bisbenzyloxymethyl-4,7,10-triazatridecane

HRID 1733777Notes

Reaction equation

HRID 1733777 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][NH:12][CH:13]([CH2:39][O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[CH2:14][NH:15][CH2:16][CH:17]([CH2:30][O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[NH:18][CH2:19][CH2:20][CH2:21][O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:49][C:50]([OH:52])=[O:51].[OH-:53].[Li+].Br.C[CH:57]([OH:59])[CH3:58]>O>[C:50]([CH2:49][N:12]([CH:13]([CH2:39][O:40][CH2:41][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[CH2:14][N:15]([CH2:49][C:50]([OH:52])=[O:51])[CH2:16][CH:17]([CH2:30][O:31][CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[N:18]([CH2:58][C:57]([OH:59])=[O:53])[CH2:19][CH2:20][CH2:21][O:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH2:11][CH2:10][CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([OH:52])=[O:51]

Participants

7

Reactant 5

HCID 260Hydrogen BromideHCID 3776IsopropanolHCID 3939Lithium HydroxideHCID 6227Bromoacetic AcidHCID 194385051,13-Bisbenzyloxy-5,9-bisbenzyloxymethyl-4,7,10-triazatridecane

Product 1

HCID 86746667N4, N7, N10-Triscarboxymethyl-1,13-bisbenzyloxy-5,9-bisbenzyloxymethyl-4,7,10-triazatridecane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,13-Bisbenzyloxy-5,9-bisbenzyloxymethyl-4,7,10-triazatridecane (0.37 g, 0.6 mmol) was dissolved in 2-propanol (5 ml). A solution of bromoacetic acid (0.33 g, 2.4 mmol), lithium hydroxide (0.10 g 2.4 mmol) in water (20 ml) was added. The temperature was gradually increased to reflux over five hours and kept at reflux for four hours. The reaction mixture was kept in the alkaline range during the alkylation. The solution was neutralised with concentrated hydrobromic acid and chromatographed on silica. N4,N7,N10 -Triscarboxymethyl-1,13-bisbenzyloxy-5,9-bisbenzyloxymethyl-4,7,10-triazatridecane was isolated as a white solid. Yield 0.30 g (70%) m.p. 150° C. The structure was confirmed by 1H NMR and 13C NMR.

Workup

  1. temperatureThe temperature was gradually increased
  2. temperatureto reflux over five hours
  3. temperatureat reflux for four hours
  4. customchromatographed on silica

Sources & evidence

ORD record
ord-4e90ad84cd434acead41baad7cb44d77
Source dataset
uspto-grants-1996_07
Patent number
US05531978

Reaction notes

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