Sodium Methoxide → HCID 68939219, compound

HRID 2189434Notes

Reaction equation

HRID 2189434 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[O:24][C:25]1[C:29]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][NH:39][C:40]([O:42][CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[O:41])=[CH:33][C:32]=2[CH3:50])=[C:28]([CH:51]([CH3:53])[CH3:52])[NH:27][N:26]=1)(=O)C.C[O-].[Na+]>CO>[CH2:43]([O:42][C:40]([NH:39][CH2:38][CH2:37][C:34]1[CH:35]=[CH:36][C:31]([CH2:30][C:29]2[C:25]([O:24][C@@H:6]3[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]3[OH:4])=[N:26][NH:27][C:28]=2[CH:51]([CH3:53])[CH3:52])=[C:32]([CH3:50])[CH:33]=1)=[O:41])[C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 68940131HCID 68940131, compound

Product 1

HCID 68939219HCID 68939219, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyloxy)-4-({4-[2-(benzyloxycarbonylamino)ethyl]-2-methylphenyl)methyl}-5-isopropyl-1H-pyrazole (20 mg) was dissolved in methanol (1 mL). To the solution was added sodium methoxide (28% methanol solution, 0.005 mL), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol) to give 4-({4-[2-(benzyloxycarbonylamino)ethyl]-2-methylphenyl}methyl)-3-(β-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazole. This material was dissolved in methanol (1 mL). To the solution was added 10% palladium-carbon powder (5 mg), and the mixture was stirred at room temperature under a hydrogen atmosphere for 6 hours. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure to give the title compound (11 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. distillationthe residue was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol)

Sources & evidence

ORD record
ord-f3109f1417024ddcb8bd0682de041883
Source dataset
uspto-grants-2012_12
Patent number
US08324176B2

Reaction notes

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