Sodium Hydroxide → HCID 57802353, compound

HRID 2102324Notes

Reaction equation

HRID 2102324 reaction equation
[CH2:1]([C:8]1[C:9](=[O:19])[NH:10][N:11]([CH:16]([CH3:18])[CH3:17])[C:12]=1[CH:13]([CH3:15])[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC([O:23][CH2:24][C@H:25]1[O:30][C@H:29](Br)[C@H:28]([O:32]C(C)=O)[C@@H:27]([O:36]C(C)=O)[C@@H:26]1[O:40]C(C)=O)=O.[OH-].[Na+]>ClCCl>[CH2:1]([C:8]1[C:9]([O:19][C@@H:29]2[O:30][C@H:25]([CH2:24][OH:23])[C@@H:26]([OH:40])[C@H:27]([OH:36])[C@H:28]2[OH:32])=[N:10][N:11]([CH:16]([CH3:18])[CH3:17])[C:12]=1[CH:13]([CH3:14])[CH3:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 101776alpha-D-Glucopyranosyl bromide, tetraacetateHCID 23079532HCID 23079532, compound

Product 1

HCID 57802353HCID 57802353, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-benzyl-1,5-diisopropyl-1,2-dihydro-3H-pyrazole-3-one (0.078 g), acetobromo-α-D-glucose (0.62 g) and benzyl (n-tributyl)ammonium bromide (0.054 g) in dichioromethane (4 mL) was added a sodium hydroxide aqueous solution (5 mol/L, 0.6 mL) and the mixture was stirred at room temperature for 2 hours. The reaction mixture was purified by column chromatography on aminopropylated silica gel (eluent: tetrahydrofuran). The obtained semi purified 4-benzyl-1,5diisopropyl-3-(2,3,4,6-tetraacetyl-1β-D-glucopyranosyloxy)-1H-pyrazole was dissolved in methanol (3 mL), and sodium methoxide (28% methanol solution, 0.58 mL) was added to the solution. The mixture was stirred at room temperature for 2 hours. The solvent of the reaction mixture was removed under reduced pressure, and the residue was acidified by adding 10% citric acid aqueous solution. The mixture was purified by solid phase extraction on ODS (washing solvent: water, eluent: methanol). Further purification by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1) gave the title compound (0.11 g).

Workup

  1. customThe reaction mixture was purified by column chromatography on aminopropylated silica gel (eluent: tetrahydrofuran)
  2. customThe obtained semi purified 4-benzyl-1,5diisopropyl-3-(2,3,4,6-tetraacetyl-1β-D-glucopyranosyloxy)-1H-pyrazole
  3. dissolutionwas dissolved in methanol (3 mL)
  4. additionsodium methoxide (28% methanol solution, 0.58 mL) was added to the solution
  5. stirringThe mixture was stirred at room temperature for 2 hours
  6. customThe solvent of the reaction mixture was removed under reduced pressure
  7. additionby adding 10% citric acid aqueous solution
  8. customThe mixture was purified by solid phase extraction on ODS (washing solvent: water, eluent: methanol)
  9. customFurther purification by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1)

Sources & evidence

ORD record
ord-740e5c5de6c94182bef79747846e0a45
Source dataset
uspto-grants-2009_08
Patent number
US07576063B2

Reaction notes

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