Benzyl succinimido carbonate → 1-(benzyloxycarbonyl)-3-(beta-D-gluco-pyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-pyrazole

HRID 33130

Reaktionsgleichung

Reaktionsgleichung von HRID 33130
[C@@H:1]1([O:12][C:13]2[C:17]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH:26]([CH3:28])[CH3:27])=[CH:21][CH:20]=3)=[C:16]([CH3:29])[NH:15][N:14]=2)[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].[CH2:30]([O:37][C:38](ON1C(=O)CCC1=O)=[O:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O1CCCC1>[CH2:30]([O:37][C:38]([N:15]1[C:16]([CH3:29])=[C:17]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH:26]([CH3:27])[CH3:28])=[CH:21][CH:20]=2)[C:13]([O:12][C@@H:1]2[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]2[OH:3])=[N:14]1)=[O:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Komponenten

4

Edukt 2

HCID 83172Benzyl succinimido carbonateHCID 98015583-(beta-D-glucopyranosyloxy)-4-[(4-iso-propoxyphenyl)methyl]-5-methyl-1H-pyrazole

Produkt 1

HCID 673349881-(benzyloxycarbonyl)-3-(beta-D-gluco-pyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-pyrazoleAusbeute 75,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-(β-D-glucopyranosyloxy)-4-[(4-iso-propoxyphenyl)methyl]-5-methyl-1H-pyrazole (1.3 g) in tetrahydrofuran (30 mL) was added N-(benzyloxycarbonyloxy)-succinimide (1.6 g), and the mixture was heated under reflux overnight. The reaction mixture was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1) to give 1-(benzyloxycarbonyl)-3-(β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methylpyrazole (1.3 g).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1)

Quellen und Nachweise

ORD-Eintrag
ord-483ab3658a924a409950bacc3867d44b
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429568B2

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