HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → (S)-2,2-Difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)-1-(2-(5-((3,4,5-trimethoxyphenoxy)methyl)isoxazol-3-yl)pyrrolidin-1-yl)ethanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 3,4,5-Trimethoxyphenol | HCID 69505 | — |
| Reactant | (S)-(3-(1-(2,2-Difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)acetyl)pyrrolidin-2-yl)isoxazol-5-yl)methyl methanesulfonate | HCID 86706749 | — |
| Solvent | Water | HCID 962 | — |
| Product | (S)-2,2-Difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)-1-(2-(5-((3,4,5-trimethoxyphenoxy)methyl)isoxazol-3-yl)pyrrolidin-1-yl)ethanone | HCID 73672155 | 83.2% |
Reaction Steps
To a DMF (1.0 mL) solution of the compound (20.8 mg) obtained in Example 3-(5) and 3,4,5-trimethoxyphenol (16.0 mg), K2CO3 (24.0 mg) was added and the mixture was stirred at room temperature for 30 minutes, then at 50° C. for 2 hours. The reaction mixture was added to water (20 mL) and the organic layer extracted with AcOEt (20 mL×2) was dried (MgSO4), filtered and concentrated to give a crude product, which was further purified by PTLC(NH-form) to give the titled compound (20.5 mg, colorless amorphous.)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09181229B2 |
| Source dataset | uspto-grants-2015_11 |
| ORD ID | ord-48611e1c37c140a2b0751f9e1d79a5f4 |
| Source note | uspto-grants-2015_11 |