Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | HCID 72310557 | HCID 72310557 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 72310560 | HCID 72310560 | 96.2% |
Reaction Steps
To a solution of 6-{3-chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-propyl]-phenoxy}-4-trifluoromethyl-nicotinic acid methyl ester (Example 163, 65 mg) in tetrahydrofuran (0.5 ml) was added a 1 M aqueous sodium hydroxide solution (0.23 ml) at 0° C. The mixture was stirred at 0° C. for 30 min and at room temperature for 3 h. The mixture was cooled in an ice bath. 2 M aqueous HCl (0.12 ml) and EtOAc were added. The organic phase was dried (MgSO4), filtered and concentrated. The product was purified by chromatography (SiO2, cyclohexane/EtOAc 1:1=>EtOAc=>EtOAc/MeOH 4:1) to give the title compound (61 mg) as a colorless solid. MS (m/e)=551.3 [M+H+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08138189B2 |
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| Source dataset | uspto-grants-2012_03 |
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| ORD ID | ord-ecf8656e539e44a3b97a48741a993df0 |
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| Source note | uspto-grants-2012_03 |
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