HuagongsheHuagongshe Chemistry Print Report · For research reference only
p-Toluenesulfonic acid → 1alpha-(tert-butyldimethylsilyl)oxy-3beta-(N,N-dimethylcarbamoyl)oxypregna-5,7-diene-20-carbaldehyde
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | p-Toluenesulfonic acid | HCID 6101 | — |
| Reactant | 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1alpha-(tert-butyldimethylsilyl)oxy-3beta-(N,N-dimethylcarbamoyl)oxypregna-5,7-diene | HCID 57254932 | — |
| Solvent | Acetone | HCID 180 | — |
| Product | 1alpha-(tert-butyldimethylsilyl)oxy-3beta-(N,N-dimethylcarbamoyl)oxypregna-5,7-diene-20-carbaldehyde | HCID 86745835 | 66.6% |
Reaction Steps
In 10 ml of acetone was dissolved 110 mg of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α-(tert-butyldimethylsilyl)oxy- 3β-(N,N-dimethylcarbamoyl)oxypregna-5,7diene, followed by addition of 10 mg of p-toluenesulfonic acid. The mixture was refluxed in an atmosphere of argon gas for 4 hours. The reaction mixture was then worked up in the same manner as Example 156 to give 63 mg of 1α-(tert-butyldimethylsilyl)oxy-3β-(N,N-dimethylcarbamoyl)oxypregna-5,7-diene-20-carbaldehyde showing the following physical properties.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05359055 |
| Source dataset | uspto-grants-1994_10 |
| ORD ID | ord-9e752b8f0f44497f8c263365f493253d |
| Source note | uspto-grants-1994_10 |