Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Water | HCID 962 | — |
| Edukt | Ethyl Acetate | HCID 8857 | — |
| Edukt | Trimethylsilyldiazomethane | HCID 167693 | — |
| Edukt | HCID 178487600 | HCID 178487600 | — |
| Lösungsmittel | Methanol | HCID 887 | — |
| Lösungsmittel | Tetrahydrofuran | HCID 8028 | — |
| Produkt | HCID 178500714 | HCID 178500714 | 81% |
Reaktionsschritte
(Diazomethyl)trimethylsilane (0.6M hexane solution) (0.392 mL, 0.24 mmol) was added to a mixture of (cis-3-(((5R)-5-((7-fluoro-1,1-dimethyl-2,3-dihydro-1H-inden-5-yl)carbamoyl)-2-methoxy-7,8-dihydro-1,6-naphthyridin-6 (5H)-yl)carbonyl)cyclobutyl)acetic acid (60 mg, 0.12 mmol) in THF (1 mL) and MeOH (1 mL) at 5° C., and the mixture was stirred at room temperature for 2 hr. To the reaction mixture were added water and ethyl acetate, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 5→50% ethyl acetate/hexane) to give the title compound (50 mg, 0.095 mmol, 81%) as a colorless oil.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US09365520B2 |
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| Quelldatensatz | uspto-grants-2016_06 |
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| ORD ID | ord-1c8a11f1e2da4c22b2f316dcdeecc670 |
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| Quellennotiz | uspto-grants-2016_06 |
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