Sodium Hydroxide → HCID 57802310, compound

HRID 2102329Notes

Reaction equation

HRID 2102329 reaction equation
[CH:1]([N:4]1[C:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[C:7]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:19]=2[O:26][CH3:27])[C:6](=[O:28])[NH:5]1)([CH3:3])[CH3:2].CC([O:32][CH2:33][C@H:34]1[O:39][C@H:38](Br)[C@H:37]([O:41]C(C)=O)[C@@H:36]([O:45]C(C)=O)[C@@H:35]1[O:49]C(C)=O)=O.[OH-].[Na+]>ClCCl>[C@@H:38]1([O:28][C:6]2[C:7]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:19]=3[O:26][CH3:27])=[C:8]([C:9]3[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=3)[N:4]([CH:1]([CH3:2])[CH3:3])[N:5]=2)[O:39][C@H:34]([CH2:33][OH:32])[C@@H:35]([OH:49])[C@H:36]([OH:45])[C@H:37]1[OH:41]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 101776alpha-D-Glucopyranosyl bromide, tetraacetateHCID 66971332HCID 66971332, compound

Product 1

HCID 57802310HCID 57802310, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1-isopropyl-5-(4-methoxypheny)-4-[(2,4-dimethoxyphenyl)methyl]-1,2-dihydro-3H-pyrazole-3-one (0.090 g), acetobromo-α-D-glucose (0.48 g) and benzyl-(n-tributyl)ammonium chloride (0.037 g) in dichloromethane (2 mL) was added sodium hydroxide (5 mol/L, 0.47 mL), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was purified by column chromatography on aminopropylated silica gel (eluent:tetrahydrofuran). The obtained semi purified 1-isopropyl-5-(4-methoxyphenyl)-4-[(2,4-dimethylphenyl)-methyl]-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole was dissolved in methanol (5 mL), and sodium methoxide (28% methanol solution, 0.45 mL) was added to the solution. The mixture was stirred at room temperature overnight. The solvent of the reaction mixture was removed, and methanol (0.5 mL) and 10% citric acid aqueous solution (5 mL) were added to the residue. The mixture was purified by solid phase extraction on ODS (washing solvent:water, eluent:methanol). Further purification by preparative reverse phase column chromatography (Shiseido CAPSELLPAC C18 UG80, 5μM, 20×50 mm, flow rate 30 mL/min linear gradient, water/methanol=90/10-10/90) gave the title compound (0.065 g).

Workup

  1. customThe reaction mixture was purified by column chromatography on aminopropylated silica gel (eluent:tetrahydrofuran)
  2. customThe obtained semi purified 1-isopropyl-5-(4-methoxyphenyl)-4-[(2,4-dimethylphenyl)-methyl]-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole
  3. dissolutionwas dissolved in methanol (5 mL)
  4. additionsodium methoxide (28% methanol solution, 0.45 mL) was added to the solution
  5. stirringThe mixture was stirred at room temperature overnight
  6. customThe solvent of the reaction mixture was removed
  7. additionmethanol (0.5 mL) and 10% citric acid aqueous solution (5 mL) were added to the residue
  8. customThe mixture was purified by solid phase extraction on ODS (washing solvent:water, eluent:methanol)
  9. customFurther purification by preparative reverse phase column chromatography (Shiseido CAPSELLPAC C18 UG80, 5μM, 20×50 mm, flow rate 30 mL/min linear gradient, water/methanol=90/10-10/90)

Sources & evidence

ORD record
ord-0390b421f7764f8e9d83f0ac0109ea17
Source dataset
uspto-grants-2009_08
Patent number
US07576063B2

Reaction notes

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