Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | 2-Methoxyethanol | HCID 8019 | — |
| Reactant | HCID 68515342 | HCID 68515342 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 68511428 | HCID 68511428 | 42% |
Reaction Steps
Methyl 4-({cyclohexyl[5-(6-fluoropyridin-3-yl)-2-methylfuran-3-yl]methyl}amino)benzoate (1.9 g) was dissolved in 2-methoxyethanol (5 mL) and tetrahydrofuran (5 mL), 2N lithium hydroxide (5 mL) was added, and the mixture was stirred overnight at 80° C. The reaction mixture was poured into water, and the mixture was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (20% ethyl acetate/hexane to 40% ethyl acetate/hexane) to give the title compound (0.9 g, 42%) as an amorphous compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08309580B2 |
|---|
| Source dataset | uspto-grants-2012_11 |
|---|
| ORD ID | ord-eda977418d4c462797728d30074fc02b |
|---|
| Source note | uspto-grants-2012_11 |
|---|