Water → (S)-(-)-5-[(2-Acetoxypropanoyl)amino]-2,4,6-triiodoisophthalic Acid

HRID 76839

Reaktionsgleichung

[C:1]([O:4][C@@H:5]([CH3:9])[C:6](Cl)=[O:7])(=[O:3])[CH3:2].[NH2:10][C:11]1[C:12]([I:25])=[C:13]([C:22]([OH:24])=[O:23])[C:14]([I:21])=[C:15]([C:19]=1[I:20])[C:16]([OH:18])=[O:17].O>CC(N(C)C)=O>[C:1]([O:4][C@@H:5]([CH3:9])[C:6]([NH:10][C:11]1[C:19]([I:20])=[C:15]([C:16]([OH:18])=[O:17])[C:14]([I:21])=[C:13]([C:12]=1[I:25])[C:22]([OH:24])=[O:23])=[O:7])(=[O:3])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

(S)-1-chloro-1-oxopropan-2-yl acetate (0.75 ml, 5.91 mmol) was added drop-wise to a solution of 5-amino-2,4,6-triiodoisophthalic acid (1.0 g, 1.79 mmol) in DMA (5 ml). The resulting mixture was stirred at about 50° C. for 5 hours and 20 minutes. 80 ml of water was added to the reaction mixture at room temperature after which the suspension formed was cooled to a temperature between 0° C. and 5° C. and stirred for 25 minutes at this temperature. The suspension was filtered and the solid washed with water. The product was dried in a vacuum oven at 40° C. to yield (S)-5-(2-acetoxypropanamido)-2,4,6-triiodoisophthalic acid (0.695 g, 1.03 mmol). The MS, 1H-NMR and 13C-NMR data are consistent with the structure for (S)-5-(2-acetoxypropanamido)-2,4,6-triiodoisophthalic acid.

Aufarbeitung

customformed
temperaturewas cooled to a temperature between 0° C. and 5° C.
stirringstirred for 25 minutes at this temperature
filtrationThe suspension was filtered
washthe solid washed with water
customThe product was dried in a vacuum oven at 40° C.

Quellen und Nachweise

ORD-Eintrag: ord-ab0b12a16a294dd3a941a09e08b3714b
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08835672B2

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