Trifluoroacetic acid → 7-((R)-2-amino-3-(benzyloxy)propanoyl)-2-methyl-4-phenyl-2,7-diazaspiro[4.5]decan-1-one
Reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([NH:31]C(=O)OC(C)(C)C)[C:11]([N:13]1[CH2:30][CH2:29][CH2:28][C:15]2([C:19](=[O:20])[N:18]([CH3:21])[CH2:17][CH:16]2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:14]1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:31][C@H:10]([CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:11]([N:13]1[CH2:30][CH2:29][CH2:28][C:15]2([C:19](=[O:20])[N:18]([CH3:21])[CH2:17][CH:16]2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:14]1)=[O:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture comprising tert-butyl (2R)-3-(benzyloxy)-1-(2-methyl-1-oxo-4-phenyl-2,7-diazaspiro[4.5]decan-7-yl)-1-oxopropan-2-ylcarbamate (500 mg, 0.959 mmol) and TFA (2.215 ml, 28.8 mmol) in DCM (5 mL) was stirred at room temperature for 2 hours. The reaction mixture was concentrated in vacuo. The crude was then diluted with DCM (10 mL) and washed with a saturated solution of sodium bicarbonate (10 mL). The aqueous phase was further extracted with DCM (3×10 mL). The combined organic portions were dried (MgSO4), and concentrated under reduced pressure to afford the title compound. No purification was performed on the title compound.
Workup
- concentrationThe reaction mixture was concentrated in vacuo
- additionThe crude was then diluted with DCM (10 mL)
- washwashed with a saturated solution of sodium bicarbonate (10 mL)
- extractionThe aqueous phase was further extracted with DCM (3×10 mL)
- dry with materialThe combined organic portions were dried (MgSO4)
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-5c2dd78e0edf43bb8b6e198e425dab30
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08546416B2
Reaction notes
Loading…