HCID 68958299, compound → HCID 57566160, compound
Reaction equation
[NH2:1][C:2]([CH2:4][N:5]1[C:10](=[O:11])[CH2:9][C@@H:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[C@@:7]2([C:26]3[C:21](=[CH:22][C:23]([Br:27])=[CH:24][CH:25]=3)[NH:20][C:19]2=[O:28])[C@H:6]1[C:29]([CH3:31])=[CH2:30])=[O:3].COC([Si](C)(C)C)C>FC(F)(F)C(O)=O.ClCCl>[NH2:1][C:2]([CH2:4][N:5]1[C:10](=[O:11])[CH2:9][C@@H:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[C@@:7]2([C:26]3[C:21](=[CH:22][C:23]([Br:27])=[CH:24][CH:25]=3)[NH:20][C:19]2=[O:28])[C@H:6]1[C:29]([CH3:31])=[CH2:30])=[O:3]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
The chiral (2′R,3R,4′S)-1′-(aminocarbonyl-methyl)-6-bromo-4′-(3-chlorophenyl)-2′-isopropenyl-2,3-dihydro-2,6′-dioxospiro[indole-3,3′-piperidine]-1-methoxyethyl trimethylsilane (27 mg, 0.043 mmol) was dissolved in a solution of trifluoroacetic acid (2 mL) in dichloromethane (5 mL). The reaction mixture was stirred at room temperature for 0.5 h, then concentrated. The residue was dissolved in a solution of methanol (3 mL) and N,N′-diisopropylethylamine (1 mL). The reaction tube was then placed into the cavity of a focused monomode microwave reactor and the contents of the flask were irradiated at 120° C. for 30 min. The reaction mixture was concentrated and the residue was purified by Prep-HPLC to give title compound (20 mg, 93%) m/z (M+H)+: 502
Workup
- concentrationconcentrated
- dissolutionThe residue was dissolved in a solution of methanol (3 mL) and N,N′-diisopropylethylamine (1 mL)
- customThe reaction tube was then placed into the cavity of a focused monomode microwave reactor
- customthe contents of the flask were irradiated at 120° C. for 30 min
- concentrationThe reaction mixture was concentrated
- customthe residue was purified by Prep-HPLC
Sources & evidence
- ORD record
- ord-5a8d015acfda42dfb9ed7563facf515f
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07495007B2
Reaction notes
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