Sodium Methoxide → 4-(2-Benzyloxybenzyl)-3-(beta-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazole

HRID 1351095Notes

Reaction equation

HRID 1351095 reaction equation
[CH:1]([C:4]1[NH:8][N:7]=[C:6]([O:9][C@@H:10]2[O:27][C@H:26]([CH2:28][O:29]C(=O)C)[C@@H:21]([O:22]C(=O)C)[C@H:16]([O:17]C(=O)C)[C@H:11]2[O:12]C(=O)C)[C:5]=1[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([CH3:3])[CH3:2].C[O-].[Na+]>O1CCCC1.CO>[CH2:41]([O:40][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=1[CH2:33][C:5]1[C:6]([O:9][C@@H:10]2[O:27][C@H:26]([CH2:28][OH:29])[C@@H:21]([OH:22])[C@H:16]([OH:17])[C@H:11]2[OH:12])=[N:7][NH:8][C:4]=1[CH:1]([CH3:3])[CH3:2])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 695166955-isopropyl-4-(2-benzyloxybenzyl)-3-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-1H-pyrazole

Product 1

HCID 99569754-(2-Benzyloxybenzyl)-3-(beta-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazole

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4-(2-benzyloxybenzyl)-5-isopropyl-1,2-dihydropyrazol-3-one (114 mg) and acetobromo-α-D-glucose (173 mg) in acetonitrile (2 mL) was added silver carbonate (127 mg), and the mixture was stirred under shading the light at room temperature for 3 days. The reaction mixture was purified by column chromatography on aminopropyl silica gel (eluent: ethyl acetate/hexane=1/1) to give 5-isopropyl-4-(2-benzyloxybenzyl)-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole. To a solution of 5-isopropyl-4-(2-benzyloxybenzyl)-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole in tetrahydrofuran (1 mL) and methanol (0.5 mL) was added sodium methoxide (28% methanol solution, 50 μL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1-5/1) to give the title compound (22 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1-5/1)

Sources & evidence

ORD record
ord-1dcdd00a11de4691b10bdbda4d82ce27
Source dataset
uspto-grants-2007_05
Patent number
US07217697B2

Reaction notes

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