HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ammonium Hydroxide → Sitagliptin enamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ammonium Hydroxide | HCID 14923 | — |
| Reactant | Ammonium Acetate | HCID 517165 | — |
| Reactant | 1-(3-(trifluoromethyl)-5,6-dihydro(1,2,4)triazolo(4,3-a)pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione | HCID 9887588 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | Sitagliptin enamine | HCID 29986152 | — |
Reaction Steps
A 5 L round-bottom flask was charged with methanol (100 mL), the ketoamide 2-3 (200 g), and ammonium acetate (110.4 g). Methanol (180 mL) and 28% aqueous ammonium hydroxide (58.6 mL) were then added keeping the temperature below 30° C. during the addition. Additional methanol (100 mL) was added to the reaction mixture. The mixture was heated at reflux temperature and aged for 2 h. The reaction was cooled to room temperature and then to about 5° C. in an ice-bath. After 30 min, the solid was filtered and dried to afford 2-4 as a solid; m.p. 271.2° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07495123B2 |
| Source dataset | uspto-grants-2009_02 |
| ORD ID | ord-bab49e909a2645ffbe8e2ba9933e5f0e |
| Source note | uspto-grants-2009_02 |