Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Isopropanol | HCID 3776 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | HCID 86623991 | HCID 86623991 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 86623992 | HCID 86623992 | 92.2% |
Reaction Steps
To a mixture of tert-butyl {[5-(2-chloropyridin-3-yl)-4-fluoro-1-(phenylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (5.50 g), tetrahydrofuran (25 mL), 2-propanol (25 mL) and methanol (20 mL) was added a 1 mol/L aqueous sodium hydroxide solution (50 mL), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: hexane:ethyl acetate=1:1) to give the title compound as a yellow solid (yield 3.59 g, 92%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08933105B2 |
|---|
| Source dataset | uspto-grants-2015_01 |
|---|
| ORD ID | ord-904c4fcc36e64fe99fee97543439181d |
|---|
| Source note | uspto-grants-2015_01 |
|---|