Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium | HCID 5360545 | — |
| Reactant | Azetidon | HCID 10935078 | — |
| Reactant | HCID 178418634 | HCID 178418634 | — |
| Catalyst | Zinc bromide | HCID 10421208 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 54270161 | HCID 54270161 | 89.1% |
Reaction Steps
To a solution of 4-(R)acetoxy-3(R)-[1(R)t-butyldimethylsilyloxyethyl]azetidin-2-one (2.87 g) in dioxane (40 ml) the sodium salt of thioacetic acid (1.2 g) was added. Zinc bromide (2.7 g) was added to the resulting suspension and the reaction mixture was stirred for 4 hours at 40° C. The reaction mixture was then cooled at room temperature and poured in a mixture of ethyl acetate and water. The organic layer was separated, washed twice with water, dried over anhydrous sodium sulfate, and evaporated in vacuo. The residue was purified by column chromatography to give 2.7 g of the title product (89% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05399679 |
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| Source dataset | uspto-grants-1995_03 |
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| ORD ID | ord-9b4a28c99b1444e39d2f44663a58173e |
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| Source note | uspto-grants-1995_03 |
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