Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Sulfite | HCID 24437 | — |
| Reactant | N-bromobutanimide | HCID 67184 | — |
| Reactant | HCID 67257546 | HCID 67257546 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58456373 | HCID 58456373 | 94.7% |
Reaction Steps
The product of Step 2 (14.5 g, 48.6 mmol) was dissolved in DMF (58 mL) and then treated with NBS (11.24 g, 63.2 mmol) and warmed to 40° C. for 3 hours. The reaction was quenched with Na2SO3 (3.0 g, 24.30 mmol) in H2O (50 mL) and the solution was then extracted with EtOAc (100 mL), washed with brine (50 mL) and then chromatographed on silica gel to afford tert-butyl (4R)-4-(5-bromo-1,3-thiazol-2-yl)-4-hydroxyazepane-1-carboxylate (18.3 g, 46 mmol). MS ESI: [M+H-tBu]+ m/z 320.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08759366B2 |
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| Source dataset | uspto-grants-2014_06 |
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| ORD ID | ord-0fdef05ede12409285b0ce6f9abb5b15 |
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| Source note | uspto-grants-2014_06 |
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