Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | HCID 59331291 | HCID 59331291 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 66681631 | HCID 66681631 | 42.3% |
Reaction Steps
Ethyl (2-bromo-1,3-thiazol-4-yl)(oxo)acetate (3.07 g, 11.6 mmol) synthesized in Example (9a) was dissolved in methanol (100 mL), and cooled to 0° C. Sodium borohydride (1.32 g, 34.9 mmol) was added in small portions, and stirring was carried out at 0° C. for 1.5 hours, followed by stirring at room temperature for further 2 hours. Dilute hydrochloric acid (1M, 100 mL) was added, and the solution was separated with ethyl acetate (200 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=20%-80%) to afford the desired compound (1.10 g, yield 42%) as a yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08415359B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-7083e63be4554a8dbebbb60d71eafa85 |
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| Source note | uspto-grants-2013_04 |
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