Trifluoroacetic acid → (+/-)-2-Methyl-3-amino-N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylpropanamide
Reaction equation
[CH3:1][CH:2]([CH2:23][NH:24]C(OC(C)CC)=O)[C:3]([N:5]([CH2:10][C:11]1[CH:21]=[C:20]([Cl:22])[C:14]2[O:15][CH2:16][CH2:17][CH2:18][O:19][C:13]=2[CH:12]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])=[O:4].FC(F)(F)C(O)=O>ClCCl>[CH3:1][CH:2]([CH2:23][NH2:24])[C:3]([N:5]([CH2:10][C:11]1[CH:21]=[C:20]([Cl:22])[C:14]2[O:15][CH2:16][CH2:17][CH2:18][O:19][C:13]=2[CH:12]=1)[CH2:6][CH:7]([CH3:8])[CH3:9])=[O:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The above (±)-2-Methyl-3-(methylpropan-2-yl)oxycarbonylamino-N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylpropanamide was dissolved in dichloromethane (3 ml) and treated with trifluoroacetic acid (3 ml). After stirring for two hours at room temperature, the reaction mixture was concentrated under reduced pressure. The residue was partitioned between dichloromethane (10 mL) and aq. sodium carbonate (sat., 10 mL). The aqueous layer was extracted with dichloromethane (10 ml×2). After washing with brine, the organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure to yield a resin: MS (m+1)=355.5.
Workup
- concentrationthe reaction mixture was concentrated under reduced pressure
- customThe residue was partitioned between dichloromethane (10 mL) and aq. sodium carbonate (sat., 10 mL)
- extractionThe aqueous layer was extracted with dichloromethane (10 ml×2)
- washAfter washing with brine
- dry with materialthe organic layer was dried with anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customto yield a resin
Sources & evidence
- ORD record
- ord-b2f66c3ba5e1408ebe51e301b6913130
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08722896B2
Reaction notes
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