Cesium carbonate → 3-(beta-D-glucopyranosyloxy)-1-(2-hydroxyethyl)-5-methyl-4-[(4-cyclopropylphenyl)methyl]-1H-pyrazole

HRID 7384

Reaction equation

HRID 7384 reaction equation
[C@@H:1]1([O:12][C:13]2[C:17]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([CH:25]4[CH2:27][CH2:26]4)=[CH:21][CH:20]=3)=[C:16]([CH3:28])[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].C(=O)([O-])[O-].[Cs+].[Cs+].[C:35](OCCBr)(=[O:37])[CH3:36].[OH-].[Na+]>CN(C)C=O.CO.O>[C@@H:1]1([O:12][C:13]2[C:17]([CH2:18][C:19]3[CH:20]=[CH:21][C:22]([CH:25]4[CH2:27][CH2:26]4)=[CH:23][CH:24]=3)=[C:16]([CH3:28])[N:15]([CH2:36][CH2:35][OH:37])[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]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 135641-Acetoxy-2-bromoethaneHCID 14798Sodium HydroxideHCID 690132463-(beta-D-glucopyranosyloxy)-5-methyl-4-[(4-cyclopropylphenyl)methyl]-1H-pyrazole

Product 1

HCID 691344613-(beta-D-glucopyranosyloxy)-1-(2-hydroxyethyl)-5-methyl-4-[(4-cyclopropylphenyl)methyl]-1H-pyrazole

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 3-(β-D-glucopyranosyloxy)-5-methyl-4-[(4-cyclopropylphenyl)methyl]-1H-pyrazole (33 mg) and cesium carbonate (138 mg) in N,N-dimethylformamide (1 mL) was added 2-bromoethyl acetate (0.035 mL) at 40° C., and the mixture was stirred for 2 hours. To the reaction mixture was added water, and the mixture was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol). The obtained crude product was dissolved in methanol (1 mL), and to the solution was added 2 mol/L aqueous sodium hydroxide solution (0.04 mL), and the mixture was stirred at room temperature for 30 minutes. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on ODS (developing solvent: methanol/water=3/2) to give 3-(β-D-glucopyranosyloxy)-1-(2-hydroxyethyl)-5-methyl-4-[(4-cyclopropylphenyl)methyl]-1H-pyrazole (8 mg).

Workup

  1. distillationthe mixture was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol)
  2. customThe obtained crude product
  3. stirringthe mixture was stirred at room temperature for 30 minutes
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on ODS (developing solvent: methanol/water=3/2)

Sources & evidence

ORD record
ord-e1891c54274e463798b044aadeb68576
Source dataset
uspto-grants-2006_08
Patent number
US07087579B2

Linked notes

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