HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Triethylamine → 3-hydroxy-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(5-methyl-1,3-thiazol-2-yl)benzamide
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Triethylamine | HCID 8471 | — |
| Edukt | Triethylsilane | HCID 12052 | — |
| Edukt | 3-(benzyloxy)-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-N-(5-methyl-1,3-thiazol-2-yl)benzamide | HCID 59346933 | — |
| Katalysator | palladium(II) acetate | HCID 167845 | — |
| Lösungsmittel | Dichloromethane | HCID 6344 | — |
| Produkt | 3-hydroxy-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(5-methyl-1,3-thiazol-2-yl)benzamide | HCID 59346930 | 21,4% |
Reaktionsschritte
Triethylamine (0.11 mL, 0.79 mmol) and triethylsilane (4.88 mL, 27.3 mmol) were added to palladium (11) acetate (56 mg, 9 mol %) in DCM (14 mL) under an atmosphere of argon. The reaction was stirred for 15 mins then 3-(benzyloxy)-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-N-(5-methyl-1,3-thiazol-2-yl)benzamide (1.4 g, 2.73 mmol) in DCM (14 mL) added dropwise and stirred for a further 48 hours. The reaction was filtered through celite and the filtrate concentrated in vacuo to give a residue which was chromatographed on silica, eluting with a gradient of 50-100% ethyl acetate in isohexane, to give the desired compound (0.18 g).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US07745475B2 |
| Quelldatensatz | uspto-grants-2010_06 |
| ORD ID | ord-a834994161f4422b977882c441c78710 |
| Quellennotiz | uspto-grants-2010_06 |