HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Potassium Hydroxide → (3S,4R)-1-(allyloxycarbonyl)methyl-3-[(R)-1-(tert-butyldimethylsiloxy)ethyl]-4-triphenylmethylthio-2-azetidinone
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Potassium Hydroxide | HCID 14797 | — |
| Edukt | Dicyclohexano-18-crown-6 | HCID 85955 | — |
| Edukt | Prop-2-enyl 2-bromoacetate | HCID 527610 | — |
| Edukt | (3S,4R)-4-triphenylmethylthio-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone | HCID 13821375 | — |
| Lösungsmittel | Benzene | HCID 241 | — |
| Produkt | (3S,4R)-1-(allyloxycarbonyl)methyl-3-[(R)-1-(tert-butyldimethylsiloxy)ethyl]-4-triphenylmethylthio-2-azetidinone | HCID 11114682 | — |
Reaktionsschritte
The tritylthioazetidinone 2 is treated with 1.5 equivalents of allyl bromoacetate and powdered potassium hydroxide in benzene solvent at ambient temperature in the presence of dicyclohexyl-18-crown-6 for 4 hours. The resulting (3S,4R)-1-(allyloxycarbonyl)methyl-3-[(R)-1-(tert-butyldimethylsiloxy)ethyl]-4-triphenylmethylthio-2-azetidinone (3) is isolated by conventional means. Alternatively p-nitro-benzylbromoacetate may be substituted for allylbromoacetate.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US04675317 |
| Quelldatensatz | uspto-grants-1987_06 |
| ORD ID | ord-6912df3c3d144ff483c04ed34633bf5d |
| Quellennotiz | uspto-grants-1987_06 |