HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrofluoric Acid → (R,E)-Methyl 7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl]-3-hydroxy-5-oxohept-6-enoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrofluoric Acid | HCID 14917 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | (R,E)-Methyl 3-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl]-5-oxohept-6-enoate | HCID 22848604 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | (R,E)-Methyl 7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl]-3-hydroxy-5-oxohept-6-enoate | HCID 22848603 | 100.1% |
Reaction Steps
To a solution of 16 g of the compound 6 in 100 ml of acetonitrile is added dropwise a solution of 48% hydrogen flouride in 400 ml of acetonitrile (1:19) under ice-cooling, and the mixture is warmed to room temperature and stirred for 1.5 hours. The reaction mixture is neutralized with sodium bicarbonate and extracted with ether. The organic layer is washed with sodium chloride, dried and evaporated under reduced pressure to distil ether to give 13 g (Yield: 100%) of methyl 7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl]-(3R)-3-hydroxy-5-oxo-(E)-6-heptenate 7 as syrup.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | USRE037314E1 |
| Source dataset | uspto-grants-2001_08 |
| ORD ID | ord-cddc595e00a2409894c2cb98b9e44764 |
| Source note | uspto-grants-2001_08 |