HCID 66672949, compound → HCID 66673018, compound
Reaction equation
[C:1]([O:4][CH2:5][C@@:6]([NH:26][C:27](=[O:29])[CH3:28])([CH3:25])[CH2:7][CH2:8][C:9]1[O:10][C:11]([C:14]#[C:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:12][CH:13]=1)(=[O:3])[CH3:2]>CO.[Pd]>[C:1]([O:4][CH2:5][C@@:6]([NH:26][C:27](=[O:29])[CH3:28])([CH3:25])[CH2:7][CH2:8][C:9]1[O:10][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:12][CH:13]=1)(=[O:3])[CH3:2]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a suspension of 10% palladium-charcoal (50% wet with water) (25 mg) in methanol (1 ml) was added a solution of (2R)-1-acetoxy-2-acetylamino-2-methyl-4-[5-(5-phenylpent-1-ynyl)furan-2-yl]butane (0.1245 g, 0.32 mmol) obtained in Example (1a) in methanol (1.5 ml), and the resulting mixture was stirred at room temperature under a hydrogen atmosphere for 8 hours. After stirring, the internal atmosphere was replaced with nitrogen, and the palladium-charcoal in the reaction mixture was filtered off using celite, which was washed with ethyl acetate. The filtrate and the washings were combined and evaporated to dryness in vacuo. The residue obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (3:2) as the eluent to afford the title compound (0.1029 g, yield: 82%).
Workup
- stirringAfter stirring
- filtrationthe palladium-charcoal in the reaction mixture was filtered off
- washwas washed with ethyl acetate
- customevaporated to dryness in vacuo
- customThe residue obtained
- customwas purified by chromatography on a silica gel column
Sources & evidence
- ORD record
- ord-c0af1e04ecd443f893f682424b40a157
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08101650B2
Reaction notes
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