Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | HCID 86670640 | HCID 86670640 | — |
| Solvent | Oxolane--water (1/1) | HCID 21881883 | — |
| Product | HCID 70664571 | HCID 70664571 | 73.4% |
Reaction Steps
Lithium hydroxide (108 mg, 4.37 mmol) was added to a solution of ethyl (2R)-4-[4-(4-ethoxyphenyl)-5-fluoro-2-oxopyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)butanoate (320 mg, 0.728 mmol) in tetrahydrofuran:water (1:1, 20 mL) and the reaction was allowed to stir at rt until complete. The reaction mixture was acidified with 4 M aq HCl and extracted with EtOAc. The combined organic layers were dried (MgSO4), filtered and concentrated to afford the title compound as a solid (220 mg, 73%). MS (LCMS) m/z 412.2 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.26-1.40 (m, 3 H) 1.54 (s, 3 H) 2.07-2.26 (m, 1 H) 2.43 (d, J=6.24 Hz, 1 H) 3.14 (s, 3 H) 3.83-4.15 (m, 4 H) 6.42 (d, J=7.81 Hz, 1 H) 6.93-7.07 (m, 2 H) 7.50 (dd, J=8.68, 1.85 Hz, 2 H) 7.97 (d, J=6.83 Hz, 1 H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08779148B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-760f9dc4f777449f82b07061db66364f |
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| Source note | uspto-grants-2014_07 |
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