Potassium Carbonate → 1-acetyl-4-benzyl-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyl-oxy)-1H-pyrazole

HRID 910584Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 910584
[C:1]([N:4]1[C:8]([CH:9]([CH3:11])[CH3:10])=[C:7]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:6](=[O:19])[NH:5]1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[C:26]([O:32][C@@H:33]1[C@@H:38]([O:39][C:40](=[O:45])[C:41]([CH3:44])([CH3:43])[CH3:42])[C@H:37]([O:46][C:47](=[O:52])[C:48]([CH3:51])([CH3:50])[CH3:49])[C@@H:36]([CH2:53][O:54][C:55](=[O:60])[C:56]([CH3:59])([CH3:58])[CH3:57])[O:35][C@H:34]1Br)(=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28]>C(#N)C>[C:1]([N:4]1[C:8]([CH:9]([CH3:11])[CH3:10])=[C:7]([CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:6]([O:19][C@@H:34]2[O:35][C@H:36]([CH2:53][O:54][C:55](=[O:60])[C:56]([CH3:59])([CH3:58])[CH3:57])[C@@H:37]([O:46][C:47](=[O:52])[C:48]([CH3:49])([CH3:50])[CH3:51])[C@H:38]([O:39][C:40](=[O:45])[C:41]([CH3:42])([CH3:43])[CH3:44])[C@H:33]2[O:32][C:26](=[O:31])[C:27]([CH3:30])([CH3:28])[CH3:29])=[N:5]1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 53466083HCID 53466083, VerbindungHCID 67348858HCID 67348858, Verbindung

Produkt 1

HCID 116147111-acetyl-4-benzyl-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyl-oxy)-1H-pyrazoleAusbeute 72,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 1-acetyl-4-benzyl-1,2-dihydro-5-isopropyl-3H-pyrazol-3-one (1.26 g) in acetonitrile (20 mL) were added potassium carbonate (1.01 g) and 2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl bromide (2.96 g) under stirring at room temperature. In addition, the mixture was heated to 50° C. and stirred for 3 hours. After the completion of the reaction, the insoluble material was removed by filtration. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=10/1) to give 1-acetyl-4-benzyl-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl-oxy)-1H-pyrazole (2.68 g).

Aufarbeitung

  1. temperatureIn addition, the mixture was heated to 50° C.
  2. stirringstirred for 3 hours
  3. customAfter the completion of the reaction
  4. customthe insoluble material was removed by filtration
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=10/1)

Quellen und Nachweise

ORD-Eintrag
ord-e1d43988dbf3454290464e403d634449
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022192B2

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