Pyridine → (2,6-dioxomorpholinoethyl)-N3-(ethoxycarbonylmethyl)-3,6-diazaoctanedioic acid

HRID 2372281Notes

Reaction equation

HRID 2372281 reaction equation
C(CN(CC[N:12]([CH2:26][C:27]([OH:29])=[O:28])[CH2:13][CH2:14][N:15]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:16][C:17]([OH:19])=[O:18])CC(O)=O)(O)=O.[N:30]1C=CC=[CH:32][CH:31]=1.[C:36]([O:39][C:40](=[O:42])[CH3:41])(=[O:38])[CH3:37]>>[O:38]=[C:36]1[CH2:37][N:30]([CH2:31][CH2:32][CH:16]([N:15]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:14][CH2:13][NH:12][CH2:26][C:27]([OH:29])=[O:28])[C:17]([OH:19])=[O:18])[CH2:41][C:40](=[O:42])[O:39]1

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 54279081Aadobenate Dimeglumine Impurity 3

Product 1

HCID 54255853(2,6-dioxomorpholinoethyl)-N3-(ethoxycarbonylmethyl)-3,6-diazaoctanedioic acid

Procedure

A suspension of 21.1 g (50 mmol) of N3,N6 -bis-(carboxymethyl)-N9 -(ethoxycarbonylmethyl)-3,6,9-triaza undecanedioic acid (J. Pharm. Sci. 68, 1979, 194) in 250 ml of acetic anhydride is stirred, after the addition of 50 ml of pyridine, for 3 days at room temperature. Then the precipitate is suctioned off, it is washed three times, each time with 50 ml of acetic anhydride and it is finally stirred up for several hours with absolute diethyl ether. After suctioning off, washing with absolute diethyl ether and drying in a vacuum at 40° C., 18.0 g (=89% of theory) of a white powder with a melting point of 195°-196° C. is obtained.

Workup

  1. washit is washed three times
  2. stirringeach time with 50 ml of acetic anhydride and it is finally stirred up for several hours with absolute diethyl ether
  3. washwashing with absolute diethyl ether
  4. customdrying in a vacuum at 40° C.
  5. custom18.0 g (=89% of theory) of a white powder with a melting point of 195°-196° C. is obtained

Sources & evidence

ORD record
ord-352cb44658c34351b34aff6f955b600c
Source dataset
uspto-grants-1992_03
Patent number
US05098692

Reaction notes

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