Trifluoroacetic acid → HCID 117871509, compound
Reaction equation
[CH2:1]([NH:3][C:4]([CH:6]1[N:14]([C:15](=[O:34])[C@@H:16]([NH:20][C:21](=[O:33])[C@@H:22]([N:24](C)[C:25](=O)OC(C)(C)C)[CH3:23])[CH:17]([CH3:19])[CH3:18])[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[CH2:7]1)=[O:5])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([NH:3][C:4]([C@H:6]1[N:14]([C:15](=[O:34])[C@@H:16]([NH:20][C:21](=[O:33])[C@@H:22]([NH:24][CH3:25])[CH3:23])[CH:17]([CH3:19])[CH3:18])[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[CH2:7]1)=[O:5])[CH3:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of tert-butyl (2S)-1-((2S)-1-(2-(ethylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-methyl-1-oxobutan-2-ylamino)-1-oxopropan-2-yl(methyl)carbamate (50 mg, 105 μmol, Eq: 1.00) in DCM (1 mL) was added TFA (0.5 mL, 6.49 mmol, Eq: 61.7) and the resulting mixture was stirred at rt for 2 h. The reaction mixture was concentrated in vacuo and the residue was treated with saturated aqueous NaHCO3 (5 mL). The resulting aqueous layer was extracted with DCM (3×5 mL) and the combined organic layers were dried over MgSO4 and then concentrated in vacuo. Treatment of the resulting residue with ethyl ether and hexanes gave (S)-1-[(S)-3-methyl-2-((S)-2-methylamino-propionylamino)-butyryl]-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethylamide as a white solid (33 mg), m/z=376 (M+H).
Workup
- concentrationThe reaction mixture was concentrated in vacuo
- additionthe residue was treated with saturated aqueous NaHCO3 (5 mL)
- extractionThe resulting aqueous layer was extracted with DCM (3×5 mL)
- dry with materialthe combined organic layers were dried over MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-a411c3d6b7154965a8e0dab90446ead3
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309248B2
Reaction notes
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