Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | HCID 69620982 | HCID 69620982 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 46869363 | HCID 46869363 | — |
Reaction Steps
Tert-butyl (S)-1-(6-(1-methyl-1H-pyrazol-4-yl)indolin-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate (60.0 mg, 134 μmol) was dissolved in dichloromethane (1.5 mL) and TFA (1.50 mL, 19 mmol) was added and the solution was stirred for three hours. The reaction mixture was then concentrated to dryness and then taken up in ethyl acetate and extracted and basified with saturated sodium bicarbonate solution. The organic layer was then concentrated and the residue was dissolved in ethyl acetate and 3.0 equivalents of 1M HCl in ether solution was added forming an off-white precipitate that was filtered and washed with hexanes to give (2S)-2-amino-1-(6-(1-methyl-1H-pyrazol-4-yl)indolin-1-yl)-3-phenylpropan-1-one hydrochloride 82. MS ESI (pos.) m/e: 347.2 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08785468B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-968ac73ef7524f56af7705f57036eaf3 |
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| Source note | uspto-grants-2014_07 |
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