Reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:22][O:23][C:24]1[CH:29]=[C:28]([C:30]#[N:31])[CH:27]=[CH:26][C:25]=1I)[CH2:10][CH2:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:33]([NH:36][C:37](=[CH2:42])[C:38]([O:40][CH3:41])=[O:39])(=[O:35])[CH3:34].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:33]([NH:36][C:37](=[CH:42][C:25]1[CH:26]=[CH:27][C:28]([C:30]#[N:31])=[CH:29][C:24]=1[O:23][CH2:22][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:10][CH2:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[C:38]([O:40][CH3:41])=[O:39])(=[O:35])[CH3:34]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
5.72 g (10.4 mmol) of benzyl (4R)-4-t-butoxycarbonylamino-5-(5-cyano-2-iodophenoxy)pentanoate was stirred together with 3.0 g (21 mmol) of methyl 2-acetamidoacrylate, 2.0 g (6.6 mmol) of tris(2-methylphenyl)phosphine, 270 mg (1.1 mmol) of palladium (II) acetate and 3.54 g (35 mmol) of triethylamine in 50 ml of DMF at 100° C. for 5 hours. The solvent was evaporated, and the residue was treated with ethyl acetate as the extracting solvent by an ordinary method and then purified by the silica gel chromatography (ethyl acetate/hexane) to obtain the title compound.
Workup
- customThe solvent was evaporated
- additionthe residue was treated with ethyl acetate as the extracting solvent by an ordinary method
- custompurified by the silica gel chromatography (ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-715fd5431d2c4d67a7b5470583916518
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06710056B2
Linked notes
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