Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Allyl bromide | HCID 7841 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | (Hexahydro-5-oxo-1,4-thiazepin-6-yl)carbamic acid, (1,1-dimethylethyl) ester | HCID 15591256 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 57722305 | HCID 57722305 | 81% |
Reaction Steps
54 mg of sodium hydride as a 60% suspension (2.24 mmol) are introduced at room temperature into a 100 ml round-bottomed flask, with stirring and under an argon atmosphere, containing 25 ml of THF and 660 mg of 52 (2.24 mmol). The medium is stirred for 1 hour and 452 mg (2.24 mmol) of allyl bromide are then added. The medium is stirred overnight, 25 ml of EtOAc and 25 ml of water are added to the reaction medium and, after separation of the phases by settling, the organic phase is washed with 20 ml of water. The organic phase is dried, filtered and then evaporated to dryness. 0.7 g of crude product is recovered, which product is chromatographed on a silica cartridge (20 g) with a 75/25 heptane/EtOAc mixture. 610 mg of product 56 are recovered (yield=81%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07550453B2 |
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| Source dataset | uspto-grants-2009_06 |
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| ORD ID | ord-c129995b32f444279b0c5011455bf75d |
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| Source note | uspto-grants-2009_06 |
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