Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl triflate | HCID 9526 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 2,6-Di-tert-butylpyridine | HCID 68510 | — |
| Reactant | HCID 86645803 | HCID 86645803 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 86645807 | HCID 86645807 | 95.4% |
Reaction Steps
The (2R,3R)-3-hydroxy-2-pentylnonanoic acid t-butyl ester (500 mg, 1.66 mmol) obtained in Production Example C-3 was dissolved in anhydrous dichloromethane (5.0 ml). Then, 2,6-di-t-butylpyridine (476 mg, 2.49 mmol) was added thereto to be stirred for 5 minutes at room temperature. Methyl triflate (328 mg, 1.99 mmol) was added to the obtained mixture, which was heated to 40° C. and stirred for 20 hours. An aqueous saturated ammonium chloride solution was added to the reaction solution, which was extracted 3 times with dichloromethane. The resulting organic layer was dried with anhydrous magnesium sulfate, filtered, and condensed. The obtained residue was purified by column chromatography (silica gel: 25 g, n-hexane/ethyl acetate=20/1) to produce the target compound (498 mg, 95%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08163713B2 |
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| Source dataset | uspto-grants-2012_04 |
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| ORD ID | ord-cb8d5ebeae244b91b6ac4a039057da98 |
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| Source note | uspto-grants-2012_04 |
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