Iodixanol → 5-Acetamido-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide

HRID 1477083

Reaktionsgleichung

[CH3:1][C:2]([N:4]([C:10]1[C:11]([I:34])=[C:12]([C:26]([NH:28][CH2:29][CH:30]([OH:33])[CH2:31][OH:32])=[O:27])[C:13]([I:25])=[C:14]([C:17]([NH:19][CH2:20][CH:21]([OH:24])[CH2:22][OH:23])=[O:18])[C:15]=1[I:16])CC(O)CO)=[O:3].CC(N(C1C(I)=C(C(NCC(O)CO)=O)C(I)=C(C(NCC(O)CO)=O)C=1I)CC(O)CN(C(C)=O)C1C(I)=C(C(NCC(O)CO)=O)C(I)=C(C(NCC(O)CO)=O)C=1I)=O.NC1C(I)=C(C(NCC(O)CO)=O)C(I)=C(C=1I)C(NCC(O)CO)=O>>[C:2]([NH:4][C:10]1[C:15]([I:16])=[C:14]([C:17]([NH:19][CH2:20][CH:21]([OH:24])[CH2:22][OH:23])=[O:18])[C:13]([I:25])=[C:12]([C:11]=1[I:34])[C:26]([NH:28][CH2:29][CH:30]([OH:33])[CH2:31][OH:32])=[O:27])(=[O:3])[CH3:1]

Komponenten

Edukt 3

HCID 3724Iodixanol

HCID 3730Iohexol

HCID 103950115-Amino-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide2×

Produkt 1

HCID 111153265-Acetamido-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide

Versuchsvorschrift

In the acetylation step of the industrial scale synthesis of Iohexol and Iodixanol, 5-amino-N,N′-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide (Compound B) is acetylated to produce 5-acetylamino-N,N′-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide (Compound A) using acetic anhydride as the acetylating reagent. We have now found that Compound A can be prepared from Compound B in an optimized process wherein the generation of certain impurities is significantly reduced.

Quellen und Nachweise

ORD-Eintrag: ord-c56a76d4aa0a42eeb6f43570e650ee07
Quelldatensatz: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09403757B2

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