Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Sodium Methoxide | HCID 10942334 | — |
| Reactant | HCID 23529054 | HCID 23529054 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 10195267 | HCID 10195267 | 92% |
Reaction Steps
25% Sodium methoxide solution in methanol (0.027 ml, 0.117 mmol) is added to methanesulfonic acid 4-(2-{4-[5-(acetylaminomethyl)-2-oxo-oxazolidin-3-yl]-2-fluorophenyl}-5-oxo-5,6-dihydro-4H-[1,3,4]thiadiazin-6-yl)-phenyl ester (0.050 g, 0.0932 mmol) in methanol (2 ml) and the mixture is stirred at room temperature overnight. The reaction mixture is neutralized with acetic acid (0.020 ml), evaporated to dryness and the residue is purified by PTLC (10% MeOH/DCM) to give product as a white solid (0.039 g, 92%); 1H NMR (300 MHz, DMSO-d6) δ 1.80 (s, 3H), 3.40-3.45 (bs, 2H), 3.74 (dd, J=6.9, 10.5 Hz, 1H), 4.12 (t, J=9.3 Hz, 1H), 4.70-4.79 (m, 1H), 4.98 (s, 3H), 6.73 (d, J=8.4 Hz, 2H), 7.08 (d, J=8.7 Hz, 1H), 7.37 (dd, J=1.8, 8.7 Hz, 1H), 7.55-7.60 (m, 2H), 8.25 (t, J=5.7 Hz, 1H); mp >200 (decomp.); MS (m/z): [M+H]+=459.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06828317B2 |
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| Source dataset | uspto-grants-2004_12 |
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| ORD ID | ord-1efdfeee77034f14a3faa7fa6f6f9ceb |
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| Source note | uspto-grants-2004_12 |
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