Pyridine → (2,6-dioxomorpholinoethyl)-N6-(ethoxycarbonylmethyl)-3,6-diazaoctanedioic acid

HRID 1975242Notes

Reaction equation

HRID 1975242 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:26]([NH:12][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])[C:27]([OH:29])=[O:28])[CH2:41][C:40](=[O:42])[O:39]1

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 54279081Aadobenate Dimeglumine Impurity 3

Product 1

HCID 21192212(2,6-dioxomorpholinoethyl)-N6-(ethoxycarbonylmethyl)-3,6-diazaoctanedioic acid

Procedure

A suspension of 21.2 g (50 mmol) of N3,N6 -bis-(carboxymethyl)-N9 -(ethoxycarbonylmethyl)-3,6,9-triazaundecanedioic acid (J. Pharm. Sci. 68, 1979, 194) in 250 ml of acetic anhydride is stirred, after the addition of 42.2 ml of pyridine, for three days at room temperature. Then the precipitate is suctioned off, it is washed three times, each time with 50 ml of acetic anhydride and then stirred up for several hours with absolute diethylether. After suctioning off, washing with absolute diethylether 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 then stirred up for several hours with absolute diethylether
  3. washwashing with absolute diethylether
  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-c48626ab235b4cf58bd121c811d553cc
Source dataset
uspto-grants-1994_02
Patent number
US05284647

Reaction notes

Loading…