Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | ethyl 2-((3R)-1-(2-hydroxy-2-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)ethyl)piperidin-3-yl)acetate | HCID 67168451 | — |
| Solvent | Water | HCID 962 | — |
| Product | Hydrochloric Acid | HCID 313 | 70.3% |
| Product | 2-((3R)-1-(2-hydroxy-2-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)ethyl)piperidin-3-yl)acetic acid | HCID 67169957 | — |
Reaction Steps
To ethyl 2-((3R)-1-(2-hydroxy-2-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)ethyl)piperidin-3-yl)acetate (Preparation 19A, 125 mg, 0.210 mmol were added acetonitrile (3 mL) and 6N hydrochloric acid (3 mL). The reaction mixture was heated at 60° C. for 4 h. The reaction mixture was concentrated under reduced pressure to yield a solid. To the solid was added acetonitrile (0.5 mL) and water (10 mL). The contents were sonicated and lyophilized to yield 2-((3R)-1-(2-hydroxy-2-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)ethyl)piperidin-3-yl)acetic acid, hydrochloric acid (150 mg, 0.248 mmol, 70.3% yield) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09216972B2 |
|---|
| Source dataset | uspto-grants-2015_12 |
|---|
| ORD ID | ord-cb69998140624ab2a0ab5d35710f5ac5 |
|---|
| Source note | uspto-grants-2015_12 |
|---|