HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → N-(6-(2-chlorophenyl)-5-(4-chlorophenyl)-2-(2-hydroxy-2-methylpropanoyl)furo[2,3-b]pyridin-3-yl)-2-hydroxyacetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Methanol | HCID 887 | — |
| Reactant | Lithium hydroxide, monohydrate | HCID 168937 | — |
| Reactant | 2-{[6-(2-Chlorophenyl)-5-(4-chlorophenyl)-2-(2-hydroxy-2-methylpropanoyl)furo[2,3-b]pyridin-3yl]amino}-2-oxoethyl acetate | HCID 21984913 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | N-(6-(2-chlorophenyl)-5-(4-chlorophenyl)-2-(2-hydroxy-2-methylpropanoyl)furo[2,3-b]pyridin-3-yl)-2-hydroxyacetamide | HCID 10028888 | — |
Reaction Steps
Lithium hydroxide-H2O (0.293 g), the product of Step A (3.78 g), and methanol (8.4 mL) were combined in 245 mL of THF and stirred at room temperature. After 5 min 0.50 mL of acetic acid was added and the solution concentrated. The residue was diluted with ethyl acetate and this solution washed two times with aqueous sodium bicarbonate. The solution was concentrated and purified via flash chromatography on silica gel with a gradient elution of 0 to 55% ethyl acetate in methylene chloride. The product was then further purified by recrystallization from ethanol to afford the title compound. HPLC/MS: 499.0 (M+1), 500.8 (M+3); Rt=3.77 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07091216B2 |
| Source dataset | uspto-grants-2006_08 |
| ORD ID | ord-2587e99f20af4b9a95cc53879079e3af |
| Source note | uspto-grants-2006_08 |