HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium → (2R,4R)-2-(4-(4-chlorobenzyl)-5-methyl-4H-1,2,4-triazol-3-yl)-4-hydroxy-N-((S)-7-(trifluoromethyl)chroman-4-yl)pyrrolidine-1-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium | HCID 5462222 | — |
| Reactant | (3R,5R)-1-(((S)-7-(trifluoromethyl)chroman-4-yl)carbamoyl)-5-(4-(4-chlorobenzyl)-5-methyl-4H-1,2,4-triazol-3-yl)pyrrolidin-3-yl acetate | HCID 68811435 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | (2R,4R)-2-(4-(4-chlorobenzyl)-5-methyl-4H-1,2,4-triazol-3-yl)-4-hydroxy-N-((S)-7-(trifluoromethyl)chroman-4-yl)pyrrolidine-1-carboxamide | HCID 57650462 | — |
Reaction Steps
To a solution of crude (3R,5R)-1-(((S)-7-(trifluoromethyl)chroman-4-yl)carbamoyl)-5-(4-(4-chlorobenzyl)-5-methyl-4H-1,2,4-triazol-3-yl)pyrrolidin-3-yl acetate from Step F (120 mg, 0.21 mmol) in aqueous MeOH (2.0 ml, 1:1 water:MeOH) was added potassium carbonated (116 mg, 0.84 mmol). The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was concentrated and the residue dissolved in EtOAc, washed with 1N HCl and then concentrated. Preparative HPLC purification provided the desired compound as a white fluffy solid (47 mg, 72% over 3 steps).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08288371B2 |
| Source dataset | uspto-grants-2012_10 |
| ORD ID | ord-33e8170ede2b47aabe2b15ed50f658d3 |
| Source note | uspto-grants-2012_10 |