HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → (S)-methyl 5-(4-(benzyloxy)phenyl)-3,4-dihydro-2H-pyrrole-2-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | methyl (2S)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-5-oxo-5-{4-[(phenylmethyl)oxy]phenyl}pentanoate | HCID 59164841 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (S)-methyl 5-(4-(benzyloxy)phenyl)-3,4-dihydro-2H-pyrrole-2-carboxylate | HCID 59164837 | 91% |
Reaction Steps
To a solution of methyl (2S)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-5-oxo-5-{4-[(phenylmethyl)oxy]phenyl}pentanoate (D2, 323 mg, 0.75 mmol) in dry DCM (4 ml) at 0° C., under nitrogen atmosphere was added trifluoroacetic acid (1 ml) dropwise. The resulting pale pink solution was allowed to warm to room temperature over 1 hour, then it was evaporated under reduced pressure, affording the title compound (D7, 291 mg, 0.68 mmol, 91%) as a greenish oil which may be used in the next step without any further purification; Rt (HPLC): 3.69 min; MS: (ES/+) m/z: 310 [MH+], C19H19NO3 requires 309.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08153681B2 |
| Source dataset | uspto-grants-2012_04 |
| ORD ID | ord-cf36a5a7873149eb8d43411144ae3e33 |
| Source note | uspto-grants-2012_04 |