Dimethylformamide → HCID 49873137, compound
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:22](=[O:23])[C:21]3[C:20]([C:24]([OH:26])=O)=[CH:19][CH:18]=[CH:17][C:16]=3[CH:15]2[CH3:27])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N:29](C)C=O.C(N(CC)C(C)C)(C)C>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:22](=[O:23])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][C:20]=3[C:24](=[O:26])[NH2:29])[CH:15]2[CH3:27])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
Procedure
To an orange solution of 2-(1-tert-butoxycarbonyl-piperidin-4-yl)-1-methyl-3-oxo-2,3-dihydro-1H-isoindole-4-carboxylic acid (3.8 g, 10.3 mmol) in N,N-dimethylformamide (60 mL) hydroxybenzotriazole ammonium salt (3.15 g, 20.7 mmol), 1-ethyl-3-(3′-dimethylamino) carbodiimide hydrochloric acid salt (3.34 g, 20.7 mmol) and N,N-diisopropylethylamine (5.3 mL, 30.9 mmol) were added. The reaction mixture was stirred at room temperature overnight. The solvent was removed under reduce pressure and the residue was dissolved in ethyl acetate. The solution was washed twice with sodium carbonate saturated aqueous solution, and the organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo. The crude was purified by flash chromatography (dichloromethane/methanol: 97:3) to afford the title compound (2.86 g, 74%) as a white solid.
Workup
- customThe solvent was removed
- dissolutionthe residue was dissolved in ethyl acetate
- washThe solution was washed twice with sodium carbonate saturated aqueous solution
- dry with materialthe organic phase was dried over anhydrous sodium sulfate
- concentrationconcentrated in vacuo
- customThe crude was purified by flash chromatography (dichloromethane/methanol: 97:3)
Sources & evidence
- ORD record
- ord-eed9520d44b8456cb842369ba4fccac1
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08765972B2
Reaction notes
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