Hydrochloric Acid → 2,3-Dihydroxybutanedioic Acid

HRID 2076718

Reaktionsgleichung

Reaktionsgleichung von HRID 2076718
[C:1]([OH:10])(=[O:9])[C@@H:2]([C@H:4]([C:6]([OH:8])=[O:7])[OH:5])[OH:3].[ClH:11].[CH3:12][CH2:13][CH:14]([N:16]1[N:21]=[CH:20][N:19]([C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH2:33][CH2:32][N:31]([C:34]4[CH:39]=[CH:38][C:37]([O:40][CH2:41][C@@H:42]5[O:46][C@:45]([C:53]6[CH:58]=[CH:57][C:56]([Cl:59])=[CH:55][C:54]=6[Cl:60])([CH2:47][N:48]6[N:52]=[CH:51][N:50]=[CH:49]6)[O:44][CH2:43]5)=[CH:36][CH:35]=4)[CH2:30][CH2:29]3)=[CH:24][CH:23]=2)[C:17]1=[O:18])[CH3:15].COC(C)(C)C>O1CCOCC1>[CH3:12][CH2:13][CH:14]([N:16]1[N:21]=[CH:20][N:19]([C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH2:33][CH2:32][N:31]([C:34]4[CH:39]=[CH:38][C:37]([O:40][CH2:41][C@@H:42]5[O:46][C@:45]([C:53]6[CH:58]=[CH:57][C:56]([Cl:59])=[CH:55][C:54]=6[Cl:60])([CH2:47][N:48]6[N:52]=[CH:51][N:50]=[CH:49]6)[O:44][CH2:43]5)=[CH:36][CH:35]=4)[CH2:30][CH2:29]3)=[CH:24][CH:23]=2)[C:17]1=[O:18])[CH3:15].[ClH:11].[C:1]([OH:10])(=[O:9])[CH:2]([CH:4]([C:6]([OH:8])=[O:7])[OH:5])[OH:3]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 15413tert-Butyl methyl etherHCID 55283ItraconazoleHCID 444305L-Tartaric acid

Produkt 2

HCID 8752,3-Dihydroxybutanedioic AcidHCID 11434139Itraconazole hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

Co-crystals of itraconazole HCl and tartaric acid were prepared. Approximately 212.7 mg of L-tartaric acid and 118 microL of 37% HCl were dissolved in 25 mL of hot dioxane. This solution was added to 1.0 g of cis-itraconazole dissolved in 50 mL of hot dioxane with stirring. The mixture was heated until a clear solution formed and was then allowed to cool to room temperature. Upon cooling, 50 mL tert-butyl methyl ether was added and the crystals were harvested by vacuum filtration on a Buchner funnel with #4 Whatman filter paper. The crystals were washed 3 times with 5 mL aliquots of cold tert-butyl methyl ether and left to air dry. Approximately 573 mg of a crystalline form of cis-itraconazole HCl-tartaric acid (1:1:0.5) co-crystal were obtained. (See FIGS. 20 and 21)

Aufarbeitung

  1. temperatureThe mixture was heated until a clear solution
  2. customformed
  3. temperatureUpon cooling
  4. filtrationthe crystals were harvested by vacuum filtration on a Buchner funnel with #4 Whatman
  5. filtrationfilter paper
  6. washThe crystals were washed 3 times with 5 mL aliquots of cold tert-butyl methyl ether
  7. waitleft to air
  8. customdry

Quellen und Nachweise

ORD-Eintrag
ord-e7ffca1b8a794dc2afbb6d3f2ae1018f
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07927613B2

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