p-Aminoacetophenone → HCID 17539973, compound
Reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1)=[O:3].[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.[C:33]([N:40]1[CH2:48][CH2:47][CH:43]([C:44](O)=[O:45])[CH2:42][CH2:41]1)([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34].CCN(C(C)C)C(C)C>CN(C=O)C>[C:36]([O:35][C:33]([N:40]1[CH2:48][CH2:47][CH:43]([C:44](=[O:45])[NH:10][C:7]2[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH3:1])=[CH:5][CH:6]=2)[CH2:42][CH2:41]1)=[O:34])([CH3:39])([CH3:38])[CH3:37]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 4-aminoacetophenone (6.76 g, 50 mmol) in DMF (250 ml) were added TOTU (16.40 g, 50 mmol), boc-isonipecotic acid (11.46 g, 50 mmol) and DIPEA (8.6 ml, 50 mmol). The reaction mixture was stirred at ambient temperature for 12 h. The solvent was removed in vacuo. The residue was redissolved in ethyl acetate (250 ml) and washed with sat. sodium hydrogen carbonate solution (2×50 ml), hydrochloric acid (1 N, 50 ml) and brine (50 ml). The organic phase was dried over sodium sulfate, evaporated and recrystallized from ethyl acetate. The product was obtained as white crystalline solid (yield: 12.2 g, 70%).
Workup
- customThe solvent was removed in vacuo
- dissolutionThe residue was redissolved in ethyl acetate (250 ml)
- washwashed with sat. sodium hydrogen carbonate solution (2×50 ml), hydrochloric acid (1 N, 50 ml) and brine (50 ml)
- dry with materialThe organic phase was dried over sodium sulfate
- customevaporated
- customrecrystallized from ethyl acetate
Sources & evidence
- ORD record
- ord-942a1b145372435a9e75c1f6b238f45f
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08143242B2
Reaction notes
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