HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Methoxide → 4-[(4-{3-[N-Benzyl-N-(2-carbamoylethyl)amino]-propoxy}-2-methylphenyl)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-{3-[N-benzyl-N-(2-carbamoylethyl)-amino]propoxy}-2-methylphenyl)methyl]-5-isopropyl-1H-pyrazole | HCID 68945204 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | 4-[(4-{3-[N-Benzyl-N-(2-carbamoylethyl)amino]-propoxy}-2-methylphenyl)methyl]-3-(beta-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazole | HCID 68941312 | 93% |
Reaction Steps
To a solution of 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-[(4-{3-[N-benzyl-N-(2-carbamoylethyl)-amino]propoxy}-2-methylphenyl)methyl]-5-isopropyl-1H-pyrazole (45.3 g) in methanol (400 mL) was added sodium methoxide (28% methanol solution, 2.2 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 column chromatography on silica gel (eluent: dichloromethane/methanol=5/1-4/1) to give the title compound (33.2 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07635684B2 |
| Source dataset | uspto-grants-2009_12 |
| ORD ID | ord-55efd1df29e64241b0fd12bf6533f8e7 |
| Source note | uspto-grants-2009_12 |