HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → (3S)-3-Amino-1-methyl-3-[3-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]prop-2-ynyl]pyrrolidin-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | tert-Butyl N-[(3S)-1-methyl-2-oxo-3-[3-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]prop-2-ynyl]pyrrolidin-3-yl]carbamate | HCID 90015348 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (3S)-3-Amino-1-methyl-3-[3-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]prop-2-ynyl]pyrrolidin-2-one | HCID 90015136 | 77.6% |
Reaction Steps
Trifluoroacetic acid (2 mL, 26.9 mmol) was added to a solution of tert-butyl N-[(3S)-1-methyl-2-oxo-3-[3-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]prop-2-ynyl]pyrrolidin-3-yl]carbamate (which may be prepared as described in Description 7) (555 mg, 1.17 mmol) in dichloromethane (10 mL) at 20° C. and the reaction was stirred for 1 hr. The reaction was quenched by the addition of sat. NaHCO3 and the phases were separated. The organic layer was dried (Na2SO4) and the solvent evaporated to afford the (3S)-3-amino-1-methyl-3-[3-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]prop-2-ynyl]pyrrolidin-2-one (D8) (340 mg, 0.9082 mmol, 77.6% yield) as a yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09309254B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-4c17711eaa2343438da946c082605fd7 |
| Source note | uspto-grants-2016_04 |