Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Reactant | tert-Butyl 3-(4-(2-(5,5-bis(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazol-3-yl)-4-hydroxyphenyl)piperidin-1-yl)propanoate | HCID 118292878 | — |
| Reactant | HCID 178479379 | HCID 178479379 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 178451094 | HCID 178451094 | 55.5% |
Reaction Steps
4-Carbamimidamidobenzoyl chloride hydrochloride (23.57 mg) was added to a mixture of tert-butyl 3-(4-(2-(5,5-bis(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazol-3-yl)-4-hydroxyphenyl)piperidin-1-yl)propanoate (60.7 mg), pyridine (0.2 mL), and NMP (0.2 mL) at 50 C, and the obtained mixture was stirred at 50 C for 30 minutes. 4-Carbamimidamidobenzoyl chloride hydrochloride (23.57 mg) was further added thereto, and the obtained mixture was stirred at 50 C for 30 minutes. 4-Carbamimidamidobenzoyl chloride hydrochloride (23.57 mg) was further added thereto, and the obtained mixture was stirred at 50 C for 30 minutes. 4-Carbamimidamidobenzoyl chloride hydrochloride (23.57 mg) was further added thereto, and the obtained mixture was stirred overnight at 50 C. To the reaction mixture, acetonitrile was added. The precipitate was filtered off, and then, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane, subsequently methanol/ethyl acetate) to obtain the title compound (42.7 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09428470B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-5300887d748f4c7882a7cc4c60d30a8f |
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| Source note | uspto-grants-2016_08 |
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