Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | Isopropanol | HCID 3776 | — |
| Reactant | HCID 178474856 | HCID 178474856 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 178474859 | HCID 178474859 | 77.7% |
Reaction Steps
To a stirred suspension of N-{[(5S)-3-(2-fluoro-4′-{[(1H-1,2,3-triazol-5-ylmethyl)amino]methyl}biphenyl-4-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide (50.5 mg, 0.115 mmol) in methanol (1.2 mL) was added 0.5 M sulfuric acid in isopropanol (0.64 mL, 0.32 mmol) and the resulting mixture heated to 55° C. to give an almost clear solution. The resulting mixture was cooled to room temperature and stirred for an additional 2 h. The resulting solid was filtered, washed with methyl tert-butyl ether (0.5 mL) and dried under reduced pressure at 50° C. to afford the title compound (48 mg, 77.7%) as a crystalline solid which was characterized by XRPD. FIG. 6 shows a characteristic X-ray powder diffraction (XRPD) pattern of crystalline N-{[(5S)-3-(2-fluoro-4′-{[(1H-1,2,3-triazol-5-ylmethyl)amino]methyl}biphenyl-4-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide monosulfate. Characteristic peaks, expressed in degrees 2θ, are listed in Table 4.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09126991B2 |
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| Source dataset | uspto-grants-2015_09 |
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| ORD ID | ord-1b52a684e4c94f538a1a8a377ed1eee9 |
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| Source note | uspto-grants-2015_09 |
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