HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium Hydroxide → 2-(2-(2-(2-(4-(1-(tert-Butoxycarbonylamino)ethyl)phenylamino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | Methyl 2-(2-(2-(2-(4-(1-(tert-butoxycarbonylamino)ethyl)phenylamino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetate | HCID 86712678 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2-(2-(2-(2-(4-(1-(tert-Butoxycarbonylamino)ethyl)phenylamino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetic acid | HCID 86712679 | — |
Reaction Steps
LiOH (69.0 mg, 2.86 mmol) was added to a solution of methyl 2-(2-(2-(2-(4-(1-(tert-butoxycarbonylamino)ethyl)phenylamino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetate (A65) (320 mg, 0.573 mmol) in THF (7.5 mL) and water (2.5 mL) and the resulting mixture stirred at room temperature overnight. The resulting mixture was evaporated in vacuo then the residue was partitioned between EtOAc (15 mL) and 1 M aqueous HCl. The phases were separated and the aqueous phase was extracted with EtOAc. The combined organic phases were washed with brine, dried with Na2SO4 and concentrated to give the title compound A66 (310 mg, 99%); LCMS-B: rt 8.30 min; m/z 545.4 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09266864B2 |
| Source dataset | uspto-grants-2016_02 |
| ORD ID | ord-4de4ac2c26634bc8a9d9b4b717d52904 |
| Source note | uspto-grants-2016_02 |