Sodium Hydroxide → HCID 57802341, compound

HRID 2102325Notes

Reaction equation

HRID 2102325 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]2[C:13](=[O:20])[NH:14][NH:15][C:16]=2[CH:17]([CH3:19])[CH3:18])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].CC([O:24][CH2:25][C@H:26]1[O:31][C@H:30](Br)[C@H:29]([O:33]C(C)=O)[C@@H:28]([O:37]C(C)=O)[C@@H:27]1[O:41]C(C)=O)=O.[OH-].[Na+]>ClCCl>[C@@H:30]1([O:20][C:13]2[C:12]([CH2:11][C:8]3[CH:9]=[CH:10][C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[CH:6][CH:7]=3)=[C:16]([CH:17]([CH3:19])[CH3:18])[NH:15][N:14]=2)[O:31][C@H:26]([CH2:25][OH:24])[C@@H:27]([OH:41])[C@H:28]([OH:37])[C@H:29]1[OH:33]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 101776alpha-D-Glucopyranosyl bromide, tetraacetateHCID 66971382HCID 66971382, compound

Product 1

HCID 57802341HCID 57802341, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-[(4-isobutylphenyl)methyl]-5-isopropyl-1,2-dihydro-3H-pyrazole-3-one (0.082 g), acetobromo-α-D-glucose (0.62 g) and benzyl(n-tributyl)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 5-isopropyl-4-[(4-isobutylphenyl)methyl]-3-(2,3,4,6-tetraacetyl-β-D-glucopyranosyloxy)-1H-pyrazole was dissolved in methanol (5 mL), and sodium methoxide (28% methanol solution, 0.29 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 water was added to the residue. The mixture was purified by solid phase extraction (washing solvent:water, eluent:methanol). Further purification by column chromatography on silica gel (eluent:dichloromethane/methanol=20/1-7/1) gave the title compound (0.080 g).

Workup

  1. customThe reaction mixture was purified by column chromatography on aminopropylated silica gel (eluent:tetrahydrofuran)
  2. customThe obtained semi purified 5-isopropyl-4-[(4-isobutylphenyl)methyl]-3-(2,3,4,6-tetraacetyl-β-D-glucopyranosyloxy)-1H-pyrazole
  3. dissolutionwas dissolved in methanol (5 mL)
  4. additionsodium methoxide (28% methanol solution, 0.29 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, and water
  7. additionwas added to the residue
  8. customThe mixture was purified by solid phase extraction (washing solvent:water, eluent:methanol)
  9. customFurther purification by column chromatography on silica gel (eluent:dichloromethane/methanol=20/1-7/1)

Sources & evidence

ORD record
ord-3202dfe70e46493a90efccfe6f96c018
Source dataset
uspto-grants-2009_08
Patent number
US07576063B2

Reaction notes

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