HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → (S)-N-((S)-5-((2-Chloro-1-(2-cyanophenyl)-1H-indol-3-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)-2-(methylamino)propanamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | tert-butyl (S)-1-((S)-5-((2-chloro-1-(2-cyanophenyl)-1H-indol-3-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate | HCID 131736361 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (S)-N-((S)-5-((2-Chloro-1-(2-cyanophenyl)-1H-indol-3-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)-2-(methylamino)propanamide | HCID 73055137 | 45.7% |
Reaction Steps
TFA (5 mL) was added to a solution of tert-butyl (S)-1-((S)-5-((2-chloro-1-(2-cyanophenyl)-1H-indol-3-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (130 mg, 207 μmol, Eq: 1.00) in DCM (5 mL). The mixture was stirred at RT for 16 h, then concentrated. Sat. NaHCO3 was added to the residue and the mixture was extracted with DCM. The combined organic extracts were concentrated and the residue purified by preparative TLC to give the title compound (50 mg, 43%) as a white solid. MS m/z 529 (MH+)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09394263B2 |
| Source dataset | uspto-grants-2016_07 |
| ORD ID | ord-ba0e533605f44d49936ca04c10a372d2 |
| Source note | uspto-grants-2016_07 |