Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 2,2-Difluoropropionic acid | HCID 2782825 | — |
| Reactant | HCID 66691939 | HCID 66691939 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 56933344 | HCID 56933344 | 12% |
Reaction Steps
2,2-Difluoropropionic acid (66.0 mg, 0.60 mmol) was dissolved in acetonitrile (2.0 mL), and then HOBt (75.0 mg, 0.60 mmol), WSC (115 mg, 0.60 mmol), the compound (150 mg, 0.40 mmol) obtained in Example 36 (1), and Et3N (167 μL, 1.2 mmol) were added thereto, followed by stirring at room temperature overnight. Water was added to the reaction mixture, and after extraction with chloroform, the extract was washed with water and a saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporation under reduced pressure was purified using medium pressure silica gel flash column chromatography (methanol:chloroform=1:30), thereby giving the title compound (20.0 mg, 12%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09181183B2 |
|---|
| Source dataset | uspto-grants-2015_11 |
|---|
| ORD ID | ord-bb6426f46dd34c87b9cf7cffd48b5e03 |
|---|
| Source note | uspto-grants-2015_11 |
|---|