Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Benzyl chloroformate | HCID 10387 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 66671689 | HCID 66671689 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 66671463 | HCID 66671463 | 93% |
Reaction Steps
The compound (593 mg, 0.883 mmol) obtained in Example 97a was dissolved in tetrahydrofuran (9 mL), 55% sodium hydride (42 mg, 0.971 mmol) was added under ice cooling, and the mixture was stirred under ice cooling under a nitrogen atmosphere for 15 minutes. Subsequently, benzyl chloroformate (0.19 mL, 1.32 mmol) was added, and the mixture was stirred at room temperature for 18 hours. After the reaction was completed, water was added, and ethyl acetate was further added to separate the layers. The resulting organic layer was separated, washed with saturated sodium chloride solution, and then dried with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by NH silica gel column chromatography (hexane:ethyl acetate, 1:5→1:15, v/v) to give the title compound (660 mg; yield, 93%) as a colorless oily substance.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08476253B2 |
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| Source dataset | uspto-grants-2013_07 |
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| ORD ID | ord-c115bacbca5b416aa2a04c63512f94e8 |
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| Source note | uspto-grants-2013_07 |
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