Sodium Methoxide → 4-[(4-{2-[(S)-1-(Carbamoyl)ethylcarbamoyl]-2-methyl-propoxy}phenyl)methyl]-3-(beta-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazole

HRID 1442387Notes

Reaction equation

HRID 1442387 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]([O:37][CH2:38][C:39]([C:42](=[O:49])[NH:43][C@H:44]([C:46](=[O:48])[NH2:47])[CH3:45])([CH3:41])[CH3:40])=[CH:33][CH:32]=2)=[C:28]([CH:50]([CH3:52])[CH3:51])[NH:27][N:26]=1)(=O)C.C[O-].[Na+]>CO>[C:46]([C@@H:44]([NH:43][C:42]([C:39]([CH3:41])([CH3:40])[CH2:38][O:37][C:34]1[CH:33]=[CH:32][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:50]([CH3:52])[CH3:51])=[CH:36][CH:35]=1)=[O:49])[CH3:45])(=[O:48])[NH2:47]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 685388053-(2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyloxy)-4-[(4-{2-[(S)-1-(carbamoyl)ethylcarbamoyl]-2-methylpropoxy}phenyl)-methyl]-5-isopropyl-1H-pyrazole

Product 1

HCID 685382244-[(4-{2-[(S)-1-(Carbamoyl)ethylcarbamoyl]-2-methyl-propoxy}phenyl)methyl]-3-(beta-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazoleYield 87.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(2,3,4,6-tetra-O-acetyl-β-D-gluco-pyranosyloxy)-4-[(4-{2-[(S)-1-(carbamoyl)ethylcarbamoyl]-2-methylpropoxy}phenyl)methyl]-5-isopropyl-1H-pyrazole (0.14 g) in methanol (4 mL) was added sodium methoxide (28% methanol solution, 0.04 mL), 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 solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol) to give the title compound (94 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-12833d126f1f45e9a382c70e15035301
Source dataset
uspto-grants-2010_02
Patent number
US07655632B2

Reaction notes

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