Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | m-Chloroperbenzoic acid | HCID 70297 | — |
| Reactant | HCID 67269424 | HCID 67269424 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 44250417 | HCID 44250417 | 79% |
Reaction Steps
3-chloroperbenzoic acid (0.04 g, 0.23 mmol) was added portionwise to a solution of N-(cyclopropylmethyl)-3-fluoro-4-methyl-5-(2-oxo-1,2,2′,3′,5′,6′-hexahydrospiro-[indole-3,4′-thiopyran]-6-yl)benzamide (example 28a, 0.10 g, 0.24 mmol) in dichloromethane (4 mL) at 0° C. The mixture was warmed to ambient temperature. After 2 hours, the mixture was cooled to 0° C. and further 3-chloroperbenzoic acid (0.04 g, 0.23 mmol) was added portionwise and the resulting mixture was stirred at room temperature for 1 additional hour. Water and dichloromethane were added, the organic layer was separated and washed with a 4% aqueous sodium hydrogen carbonate solution, dried (MgSO4) and the solvent evaporated under reduced pressure. The residue was triturated with diethyl ether to yield the title compound (0.09 g, 79%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08772288B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-3a40b6578d0649f498906d60033b2835 |
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| Source note | uspto-grants-2014_07 |
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