HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Methoxide → 4-[(4-{2-[(S)-1-(Carbamoyl)ethylcarbamoyl]-2-methyl-propoxy}phenyl)methyl]-3-(beta-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Methoxide | HCID 10942334 | — |
| Reactant | 3-(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 | HCID 68538805 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | 4-[(4-{2-[(S)-1-(Carbamoyl)ethylcarbamoyl]-2-methyl-propoxy}phenyl)methyl]-3-(beta-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazole | HCID 68538224 | 87.1% |
Reaction Steps
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).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07655632B2 |
| Source dataset | uspto-grants-2010_02 |
| ORD ID | ord-12833d126f1f45e9a382c70e15035301 |
| Source note | uspto-grants-2010_02 |