Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | HCID 54575250 | HCID 54575250 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 54575253 | HCID 54575253 | — |
Reaction Steps
To a suspension of EXAMPLE 4E (30 mg, 0.08 mmol) in tetrahydrofuran (5 mL) was added NaOH (32 mg, 0.8 mmol) in water (0.5 ml). The reaction mixture was heated at 80° C. overnight. After cooling, the reaction mixture was neutralized with 1N aqueous HCl, and concentrated. The residue was separated by HPLC (0-100% gradient CH3CN in water containing 0.1% CF3CO2H to afford the title compound. MS (DCI/NH3) m/z 346 (M+H)+; 1H NMR (300 MHz, dimethylsulfoxide-d6): δ 4.19 (s, 2H), 6.59 (d, J=5.55 Hz, 1H), 7.47 (t, J=7.54 Hz, 1H), 7.68 (d, J=7.54 Hz, 1H), 7.77 (d, J=1.59 Hz, 1H), 7.82 (d, J=7.93 Hz, 1H), 7.97 (s, 1H), 8.19 (d, J=6.74 Hz, 2H), 8.33 (d, J=1.59 Hz, 1H), 8.73 (d, J=6.35 Hz, 2H), 10.74 (d, J=5.55 Hz, 1H), 12.98 (s, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08450320B2 |
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| Source dataset | uspto-grants-2013_05 |
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| ORD ID | ord-de234c6b343745ec8478c929578b90f6 |
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| Source note | uspto-grants-2013_05 |
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