Pyridine → N3-(2,6-Dioxomorpholinoethyl)-N6-(ethoxycarbonylmethyl)-3,6-diazaoctanedioic Acid

HRID 412988Notes

Reaction equation

HRID 412988 reaction equation
[C:1]([CH2:4][N:5]([CH2:10][CH2:11][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])[CH2:6][C:7]([OH:9])=O)([OH:3])=[O:2].N1C=CC=CC=1>C(OC(=O)C)(=O)C>[O:9]=[C:7]1[CH2:6][N:5]([CH2:10][CH2:11][N: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])[CH2:26][C:27]([OH:29])=[O:28])[CH2:4][C:1](=[O:2])[O:3]1

Participants

4

Reactant 2

HCID 1049PyridineHCID 54279081Aadobenate Dimeglumine Impurity 3

Product 1

HCID 15745373N3-(2,6-Dioxomorpholinoethyl)-N6-(ethoxycarbonylmethyl)-3,6-diazaoctanedioic Acid

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A suspension of 21.1 g (50 mmol) of N3,N6-bis-(carboxymethyl)-N9-(ethoxy-carbonylmethyl)-3,6,9-triazaundecanedioic acid in 250 ml of acetic anhydride is allowed to stir for three days at room temperature after the addition of 42.2 ml of pyridine. Then, the precipitate is suctioned off, washed three times with 50 ml of acetic anhydride each and then stirred 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. washwashed three times with 50 ml of acetic anhydride each and
  2. stirringthen stirred 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-09acada7231947c598ce5a4e3771cd8d
Source dataset
uspto-grants-2003_05
Patent number
US06565830B1

Reaction notes

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