Acetate → N,N'-Bis[(2,3-dihydroxypropyl)-2-hydroxyethyl]-5-hydroxyacetamido-2,4,6-triiodoisophthalamide

HRID 1461610

Reaktionsgleichung

Reaktionsgleichung von HRID 1461610
C([O:4][CH2:5][C:6]([NH:8][C:9]1[C:10]([I:39])=[C:11]([C:28]([NH:30][CH2:31][CH:32]([CH2:34][CH:35]([OH:38])[CH2:36][OH:37])[OH:33])=[O:29])[C:12]([I:27])=[C:13]([C:25]=1[I:26])[C:14]([NH:16][CH2:17][CH:18]([CH2:20][CH:21]([OH:24])[CH2:22][OH:23])[OH:19])=[O:15])=[O:7])(=O)C.C([O-])(=O)C>O.S(=O)(=O)(O)O>[OH:24][CH:21]([CH2:22][OH:23])[CH2:20][CH:18]([OH:19])[CH2:17][NH:16][C:14](=[O:15])[C:13]1[C:25]([I:26])=[C:9]([NH:8][C:6](=[O:7])[CH2:5][OH:4])[C:10]([I:39])=[C:11]([C:28]([NH:30][CH2:31][CH:32]([CH2:34][CH:35]([OH:38])[CH2:36][OH:37])[OH:33])=[O:29])[C:12]=1[I:27]

Komponenten

5

Edukt 2

HCID 175AcetateHCID 867453315-Acetoxyacetamido-N,N'-bis[(2,3-dihydroxypropyl)-2-hydroxyethyl]-2,4,6-triiodoisophthalamide

Produkt 1

HCID 86745330N,N'-Bis[(2,3-dihydroxypropyl)-2-hydroxyethyl]-5-hydroxyacetamido-2,4,6-triiodoisophthalamideAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

5-Acetoxyacetamido-N,N'-bis[(2,3-dihydroxypropyl)-2-hydroxyethyl]-2,4,6-triiodoisophthalamide (77 g, 0.086 g-mole) is dissolved in 270 ml of hot water containing 8.2 g (0.08 g-mole) sulfuric acid. The solution is stirred and heated at 95°-100° C. to hydrolyze the acetate. At the end of the reaction, the solution is cooled to room temperature and deionized using an anionic exchange resin, IRA-93 (Rohm and Haas Co.) to remove sulfuric acid. The solution is then concentrated and the crude product is purified by preparative liquid chromatography to provide the purified desired product (51 g; 0.06 g-mole, 70% yield). The 13C nmr spectra are consistent with the structure. The HPLC purity is 99.1% (C18, H2O/MeOH; 95/5). The water solubility (w/v) is 100%; the iv LD50 in mice is 5 g I/kg (based on iodine content). Osmolality: 676 mOsm/kg (32% I); viscosity: 8.2 cps (37°), 10.0 cps (25 °) (32% I).

Aufarbeitung

  1. temperatureheated at 95°-100° C.
  2. customAt the end of the reaction
  3. customto remove sulfuric acid
  4. concentrationThe solution is then concentrated
  5. customthe crude product is purified by preparative liquid chromatography
  6. customto provide the

Quellen und Nachweise

ORD-Eintrag
ord-3e5d0ed483124381885cc3fbfb12fcee
Quelldatensatz
uspto-grants-1991_12
Patentnummer
US05075502

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