Sodium Hydroxide → 3-(beta-d-Glucopyranosyloxy)-4-[(4-methylthiophenyl)methyl]-1h-pyrazole

HRID 1365029

Reaktionsgleichung

Reaktionsgleichung von HRID 1365029
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]2[C:11](=[O:21])[NH:12][NH:13][C:14]=2C2C=CC=CC=2)=[CH:5][CH:4]=1.CC([O:25][CH2:26][C@H:27]1[O:32][C@H:31](Br)[C@H:30]([O:34]C(C)=O)[C@@H:29]([O:38]C(C)=O)[C@@H:28]1[O:42]C(C)=O)=O.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.ClCCl>[C@@H:31]1([O:21][C:11]2[C:10]([CH2:9][C:6]3[CH:5]=[CH:4][C:3]([S:2][CH3:1])=[CH:8][CH:7]=3)=[CH:14][NH:13][N:12]=2)[O:32][C@H:27]([CH2:26][OH:25])[C@@H:28]([OH:42])[C@H:29]([OH:38])[C@H:30]1[OH:34]

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 101776alpha-D-Glucopyranosyl bromide, tetraacetateHCID 669710624-[(4-Methylthiophenyl)methyl]-5-phenyl-1,2-dihydro-3h-pyrazole-3-one

Produkt 1

HCID 1785031463-(beta-d-Glucopyranosyloxy)-4-[(4-methylthiophenyl)methyl]-1h-pyrazoleAusbeute 29,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2724282Benzenemethanaminium, N,N,N-tributyl-, bromideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of 4-[(4-methylthiophenyl)methyl]-5-phenyl-1,2-dihydro-3H-pyrazole-3-one (0.087 g), acetobromo-α-D-glucose (0.62 g) and benzyltri(n-butyl)ammonium bromide (0.054 g) in dichloromethane (3 mL) was added a sodium hydroxide aqueous solution (5 mol/L, 0.9 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was purified by column chromatography on aminopropylated silica gel (eluent: tetrahydrofuran). The obtained semi purified 4-[(4-methyl-thiophenyl)methyl]-3-(2,3,4,6-tetraacethyl-β-D-gluco-pyranosyloxy)-1H-pyrazole was dissolved in methanol (5 mL), and sodium methoxide (28% methanol solution, 0.28 mL) was added to the solution. The mixture was stirred at room temperature for 2 hours. Acetic acid (0.090 g) was added to the reaction mixture, and the solvent was removed. Water (5 mL) was added to the residue, and the mixture was purified by solid phase extraction on ODS (washing solvent: water/methanol=5/1, eluent: methanol). Column chromatography on silica gel (eluent: dichloromethane/methanol=20/1-7/1) was used for further purification to give the title compound (0.033 g).

Aufarbeitung

  1. customThe reaction mixture was purified by column chromatography on aminopropylated silica gel (eluent: tetrahydrofuran)
  2. customThe obtained semi purified 4-[(4-methyl-thiophenyl)methyl]-3-(2,3,4,6-tetraacethyl-β-D-gluco-pyranosyloxy)-1H-pyrazole
  3. dissolutionwas dissolved in methanol (5 mL)
  4. additionsodium methoxide (28% methanol solution, 0.28 mL) was added to the solution
  5. stirringThe mixture was stirred at room temperature for 2 hours
  6. additionAcetic acid (0.090 g) was added to the reaction mixture
  7. customthe solvent was removed
  8. additionWater (5 mL) was added to the residue
  9. customthe mixture was purified by solid phase extraction on ODS (washing solvent: water/methanol=5/1, eluent: methanol)
  10. customColumn chromatography on silica gel (eluent: dichloromethane/methanol=20/1-7/1) was used for further purification

Quellen und Nachweise

ORD-Eintrag
ord-5eb3aa8ffe6c4ef2a29bb2b2d433bb83
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07888487B2

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