Ammonium formate → N4,N7,N10-Triscarboxymethyl-1,13-bishydroxy-5,9-bishydroxymethyl-4,7,10-triazatridecane

HRID 1733778Notes

Reaction equation

HRID 1733778 reaction equation
[C:1]([CH2:4][N:5]([CH:17]([CH2:51][O:52]CC1C=CC=CC=1)[CH2:18][N:19]([CH2:47][C:48]([OH:50])=[O:49])[CH2:20][CH:21]([CH2:38][O:39]CC1C=CC=CC=1)[N:22]([CH2:34][C:35]([OH:37])=[O:36])[CH2:23][CH2:24][CH2:25][O:26]CC1C=CC=CC=1)[CH2:6][CH2:7][CH2:8][O:9]CC1C=CC=CC=1)([OH:3])=[O:2].C([O-])=O.[NH4+]>CO.[Pd]>[C:35]([CH2:34][N:22]([CH:21]([CH2:38][OH:39])[CH2:20][N:19]([CH2:47][C:48]([OH:50])=[O:49])[CH2:18][CH:17]([CH2:51][OH:52])[N:5]([CH2:4][C:1]([OH:3])=[O:2])[CH2:6][CH2:7][CH2:8][OH:9])[CH2:23][CH2:24][CH2:25][OH:26])([OH:37])=[O:36]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 86746667N4, N7, N10-Triscarboxymethyl-1,13-bisbenzyloxy-5,9-bisbenzyloxymethyl-4,7,10-triazatridecane

Product 1

HCID 86748685N4,N7,N10-Triscarboxymethyl-1,13-bishydroxy-5,9-bishydroxymethyl-4,7,10-triazatridecane

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N4,N7,N10 -Triscarboxymethyl-1,13-bisbenzyloxy-5,9-bisbenzyloxymethyl-4,7,10-triazatridecane (0.30 g, 0.4 mmol) was dissolved in methanol (15 ml), 10% Palladium on carbon (0.3 g) and ammonium formate (0.1 g) were added and the mixture was kept at 50° C. for 16 hours. The catalyst was filtered off and washed with methanol (5 ml). The filtrate was evaporated and the title compound was isolated as a white powder. Yield 0.14 g (95%). M.p. 173°-177° C. The structure was confirmed by 1H NMR and 13CNMR.

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with methanol (5 ml)
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-5033aa686fdf4f5bbb1b0cacf9411af7
Source dataset
uspto-grants-1996_07
Patent number
US05531978

Reaction notes

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