Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 22169095 | HCID 22169095 | — |
| Reactant | HCID 178468701 | HCID 178468701 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 18469297 | HCID 18469297 | 50.2% |
Reaction Steps
To a solution of 5-ethoxycarbonyl-2-mercaptobenzoxazole (670 mg) in DMF was added 60% sodium hydride (126 mg) in oil under ice-cooling, and the mixture was stirred for 30 minutes. A solution of 3-tert-butoxycarbonylmethylaminopropyl chloride (623 mg) in DMF was added to the reaction mixture, and the mixture was stirred with heating at 60° C. for 18 hours. Ethyl acetate was added to the reaction mixture, and the organic layer was washed with water and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=4/1 v/v) to give the title compound (594 mg, yield 50%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06420561B1 |
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| Source dataset | uspto-grants-2002_07 |
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| ORD ID | ord-e131adb70ffb4c8fb10ecb63303bd8b6 |
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| Source note | uspto-grants-2002_07 |
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