HuagongsheHuagongshe Chemistry Print Report · For research reference only
tert-Butyl methyl ether → 3-[3-(tert-Butyl-dimethyl-silanyloxy)-3-phenyl-propyl]-4-(3-methoxy-phenyl)-1-(4-nitro-phenyl)-azetidin-2-on
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | tert-Butyl methyl ether | HCID 15413 | — |
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | Bistrimethylsilylacetamid | HCID 11708267 | — |
| Reactant | 3-{5-(tert-Butyl-dimethyl-silanyloxy)-2-[(4-methoxy-phenyl)-(4-nitro-phenylamino)-methyl]-5-phenyl-pentanoyl}-4-phenyl-oxazolidin-2-on | HCID 68640083 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Product | 3-[3-(tert-Butyl-dimethyl-silanyloxy)-3-phenyl-propyl]-4-(3-methoxy-phenyl)-1-(4-nitro-phenyl)-azetidin-2-on | HCID 68639713 | 70% |
Reaction Steps
A mixture comprising 6.1 g (8.6 mmol) of product 3, 7.3 ml of bistrimethylsilylacetamid, 0.5 g of Tetrabutylammoniumfluorid and 100 ml of tert -butylmethylether is stirred under a argon atmosphere for 10 h at room temperature. After finishing of the reaction 5 ml of acetic acid are added slowly by cooling with ice and evaporated. The residue is separated by chromatography on silica gel (ethylacetate/heptane=1/2). 3.3 g (70%) of product 4 is obtained in form of a light yellow compound in solid form: C31H38N2O5Si (546.74) MS (ESI+) 547.3 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07435727B2 |
| Source dataset | uspto-grants-2008_10 |
| ORD ID | ord-3243c7ba09e54be38107f97cf59edb54 |
| Source note | uspto-grants-2008_10 |