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Hydrochloric Acid → HCID 86602033, Verbindung

HRID 1869027
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1869027
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]2[C:14]([O:21][C@@H:22]3[O:48][C@H:47]([CH2:49][O:50][C:51](=[O:56])[C:52]([CH3:55])([CH3:54])[CH3:53])[C@@H:39]([O:40][C:41](=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43])[C@H:31]([O:32][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])[C@H:23]3[O:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])=[N:15][NH:16][C:17]=2[CH:18]([CH3:20])[CH3:19])=[C:8]([CH3:57])[CH:7]=1.[CH2:58]([NH:65][CH2:66][CH2:67][C:68]([NH2:70])=[O:69])[C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1.[I-].[Na+].Cl>C(#N)C.C(O)C>[CH2:58]([N:65]([CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]2[C:14]([O:21][C@@H:22]3[O:48][C@H:47]([CH2:49][O:50][C:51](=[O:56])[C:52]([CH3:55])([CH3:54])[CH3:53])[C@@H:39]([O:40][C:41](=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43])[C@H:31]([O:32][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])[C@H:23]3[O:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])=[N:15][NH:16][C:17]=2[CH:18]([CH3:20])[CH3:19])=[C:8]([CH3:57])[CH:7]=1)[CH2:66][CH2:67][C:68](=[O:69])[NH2:70])[C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 5238Sodium Iodide2×HCID 854513-BenzylaminopropionamideHCID 689441234-{[4-(3-Chloropropoxy)-2-methylphenyl]methyl}-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-1H-pyrazole

Produkt 1

HCID 86602033HCID 86602033, Verbindung
Ausbeute 61,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 4-{[4-(3-chloropropoxy)-2-methylphenyl]-methyl}-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-pyrazole (1.34 g), 3-benzylaminopropionamide (0.73 g), sodium iodide (0.24 g), ethanol (6 mL) and acetonitrile (6 mL) was stirred at 70° C. for 2 days. To the reaction mixture was added sodium iodide (0.2 g), and the mixture was further stirred at 75° C. for 24 hours. The reaction mixture was poured into 1 mol/L hydrochloric acid, and the resulting mixture was extracted with ethylacetate. The extract was washed with water, a saturated aqueous sodium hydrogen carbonate solution and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/5-dichloromethane/methanol=15/1) to give the title compound (0.97 g).

Aufarbeitung

  1. stirringthe mixture was further stirred at 75° C. for 24 hours
  2. extractionthe resulting mixture was extracted with ethylacetate
  3. washThe extract was washed with water
  4. dry with materiala saturated aqueous sodium hydrogen carbonate solution and brine, and dried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/5-dichloromethane/methanol=15/1)

Quellen und Nachweise

ORD-Eintrag
ord-f462109feae94f89a2d2523d21b9be82
Quelldatensatz
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07635684B2

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