Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium Sulfite | HCID 24437 | — |
| Reactant | N-bromobutanimide | HCID 67184 | — |
| Reactant | HCID 67249435 | HCID 67249435 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 67247653 | HCID 67247653 | 58.7% |
Reaction Steps
To a solution of the product of Step 2 (1.4 g, 4.7 mmol) in DMF (15 mL) was added NBS (0.963 g, 5.41 mmol) and the resulting solution heated to 55° C. After 60 min the reaction was cooled and a solution of sodium sulfite (500 mg) in water (30 mL) was added followed by EtOAc. The layers were separated, the aqueous layer was back extracted twice with EtOAc and the combined organics were dried with MgSO4, filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography to afford propan-2-yl-4-(5-bromo-1,3-thiazol-2-yl)-4-hydroxy-2,6 dimethylcyclohexanecarboxylate (1.04 g, 2.76 mmol) MS ESI: [M+H]+ m/z 375.9.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08759366B2 |
|---|
| Source dataset | uspto-grants-2014_06 |
|---|
| ORD ID | ord-b535212a2194423dbf77b20a3f3edd5c |
|---|
| Source note | uspto-grants-2014_06 |
|---|