Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Chloride | HCID 312 | — |
| Reactant | 2-Methoxyethanol | HCID 8019 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | tert-Butyl (4-(chloromethyl)thiazol-2-yl)carbamate | HCID 45117840 | — |
| Product | HCID 86622744 | HCID 86622744 | 46% |
Reaction Steps
A mixture of the chloride (Intermediate II, 420 mg, 1.69 mmol) and potassium carbonate (818 mg, 5.92 mmol) in 2-methoxyethanol (12 ml) was stirred for 2 hours at 90° C. TLC indicated complete conversion. The mixture was filtered through a pad of celite and the solvent was removed under vacuum. The residue was purified by column chromatography (silica gel, ethyl acetate/heptane, 25-70% gradient) to give 46% (225 mg, 781 μmol) of title compound as pale yellow oil. 1H NMR (300 MHz, CDCl3) δ 1.56 (s, 9H), 3.39 (s, 3H), 3.54-3.58 (m, 2H), 3.64-3.69 (m, 2H), 4.58 (s, 2H), 6.82 (s, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08716320B2 |
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| Source dataset | uspto-grants-2014_05 |
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| ORD ID | ord-b7a386d64a61453781a4ef0ab09394e0 |
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| Source note | uspto-grants-2014_05 |
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