Reaction equation
[CH:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][N:2]2[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([N+:19]([O-])=O)[CH:15]=2)[N:10]=1>CO.C(OCC)(=O)C.[OH-].[OH-].[Pd+2]>[CH:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[CH2:3][N:2]2[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([NH2:19])[CH:15]=2)[N:10]=1Participants
5
Procedure
The product of Step A and palladium hydroxide on carbon (1.3 g, 20% by wt) was suspended in methanol (100 mL) and ethyl acetate (100 mL). The resulting mixture was degassed then stirred under hydrogen atmosphere (balloon) for 6 h. The reaction mixture was filtered through filter aid and the solvent removed under vacuum. The resulting oil was dissolved in ethyl acetate and the solvent removed under vacuum. The resulting oil was suspended in ether and triturated until crystallization occurred. The solids were filtered and washed with ice-cold ether then dried under vacuum to afford the product as a brown solid, MS: m/z 254 (MH+), which was used without further purification
Workup
- customThe resulting mixture was degassed
- filtrationThe reaction mixture was filtered
- filtrationthrough filter aid
- customthe solvent removed under vacuum
- dissolutionThe resulting oil was dissolved in ethyl acetate
- customthe solvent removed under vacuum
- customtriturated until crystallization
- filtrationThe solids were filtered
- washwashed with ice-cold ether
- customthen dried under vacuum
Sources & evidence
- ORD record
- ord-941df1acbb1249ef9c18b030f6937c2a
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07084156B2
Linked notes
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