HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 3-(4,4'-Dichlorobiphenyl-3-yl)-8,8-difluoro-4-hydroxy-1-azaspiro[4.5]dec-3-en-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Dimethylacetamide | HCID 31374 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Reactant | Methyl 1-{[(4,4'-dichlorobiphenyl-3-yl)acetyl]amino}-4,4-difluorocyclohexanecarboxylate | HCID 86707850 | — |
| Solvent | Water | HCID 962 | — |
| Product | 3-(4,4'-Dichlorobiphenyl-3-yl)-8,8-difluoro-4-hydroxy-1-azaspiro[4.5]dec-3-en-2-one | HCID 60168410 | — |
Reaction Steps
3.20 g (5.74 mmol) of the compound from Example 8A were initially charged in a solution of 14 ml of DMA (N,N-dimethylacetamide), a solution of 9 ml of DMA and 1.69 g (2.5 eq.) of potassium tert-butoxide was added dropwise at 20° C. and the mixture was stirred at room temperature for 4 h. The mixture was poured into 200 ml of water and the reaction was adjusted to pH 2 using concentrated aqueous hydrochloric acid, and the resulting residue was filtered off with suction. Purification by flash column chromatography (silica gel; ethyl acetate/n-hexane 1:1) gave 1.50 g (52% of theory) of the title compound of melting point m.p. 156° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08946124B2 |
| Source dataset | uspto-grants-2015_02 |
| ORD ID | ord-0b226b9005804d24a12c0a54af2801a8 |
| Source note | uspto-grants-2015_02 |