Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | N-Iodosuccinimide | HCID 120273 | — |
| Reactant | HCID 178421573 | HCID 178421573 | — |
| Catalyst | Zirconium chloride (ZrCl4), (T-4)- | HCID 9856075 | — |
| Product | HCID 178421579 | HCID 178421579 | 92,312.5% |
Reaction Steps
To a solution of (R)-4-(6-(cis-4-cyclohexylcyclohexyloxy)naphthalen-2-yl)-4-methyloxazolidin-2-one (35.0 mg, 0.0000859 mol) in methylene chloride (2 mL, 0.03 mol), N-iodosuccinimide (38.6 mg, 0.000172 mol) was added, followed by zirconium tetrachloride (4.00 mg, 0.0000172 mol) at 23° C. The reaction mixture was then sonicated and stirred for 5 minutes at 23° C. TLC and LC/MS indicated a clean reaction. The majority of solvent was removed. Solid was removed via filtration through a Celite pad. The mixture was then loaded onto a column (SiO2, 4 g, 0-50% ethyl acetate/hexanes) to give a pure product (42.3 g, 92%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08269043B2 |
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| Source dataset | uspto-grants-2012_09 |
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| ORD ID | ord-f0c98dadc65b4c929aa0984d7fe6aaf6 |
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| Source note | uspto-grants-2012_09 |
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