HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium hydroxide, monohydrate → Lithium 2-(2-(2-(2-((4-(1-(tert-butoxycarbonyl)piperidin-4-yl)phenyl)-amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lithium hydroxide, monohydrate | HCID 168937 | — |
| Reactant | tert-Butyl 4-(4-((4-(2-(2-methoxy-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate | HCID 68283243 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Lithium 2-(2-(2-(2-((4-(1-(tert-butoxycarbonyl)piperidin-4-yl)phenyl)-amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetate | HCID 68282879 | — |
Reaction Steps
LiOH.H2O (0.027 g, 0.647 mmol) was added to a solution of tert-butyl 4-(4-((4-(2-(2-methoxy-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate (I47) (0.128 g, 0.214 mmol) in THF (7 mL), water (1.5 mL) and methanol (1 mL). The resulting mixture was allowed to stir at room temperature for 20 hours. The volatiles were removed in vacuo and the residue was diluted with EtOAc (50 mL) and sat. aq. NaHCO3 (50 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2×50 mL), the organic layers were combined, washed with brine (50 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to give the title compound (I48) (0.130 g) as a pale yellow viscous oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09012461B2 |
| Source dataset | uspto-grants-2015_04 |
| ORD ID | ord-e5830951f7824fad9eebafb82d4ed08e |
| Source note | uspto-grants-2015_04 |