Triethylamine → methyl 2-acetamido-3-[2-[(2R)-3-ethoxycarbonyl-2-(4-cyanobenzoylamino)propoxy]-4-cyanophenyl]acrylate

HRID 747769Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[CH:5][C:6](I)=[C:7]([CH:33]=1)[O:8][CH2:9][C@H:10]([NH:22][C:23](=[O:32])[C:24]1[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=1)[CH2:11][C:12]([O:14][CH2:15][C:16]1C=CC=CC=1)=[O:13])#[N:2].[C:35]([NH:38][C:39](=[CH2:44])[C:40]([O:42][CH3:43])=[O:41])(=[O:37])[CH3:36].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C=O>[C:35]([NH:38][C:39](=[CH:44][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:33][C:7]=1[O:8][CH2:9][C@H:10]([NH:22][C:23](=[O:32])[C:24]1[CH:25]=[CH:26][C:27]([C:30]#[N:31])=[CH:28][CH:29]=1)[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:40]([O:42][CH3:43])=[O:41])(=[O:37])[CH3:36]

Participants

Conditions

Temperature: 90 °C

Procedure

1.28 g (2.27 mmol) of benzyl (3R)-4-(5-cyano-2-iodophenoxy)-3-(4-cyanobenzoylamino)butanoate, 975 mg (6.81 mmol) of methyl 2-acetamidoacrylate, 415 mg (1.36 mmol) of tris(2-methylphenyl)phosphine, 0.95 ml (6.81 mmol) of triethylamine and 0.5 ml of dimethylformamide were dissolved in 8.0 ml of acetonitrile. 56 mg (0.23 mmol) of palladium acetate was added to the solution at room temperature, and they were stirred at 90° C. for 12 hours. The solvent was distilled off, and the residue was purified by the silica gel column chromatography (volume ratio of chloroform:methanol=30:1) to obtain the title compound.

Workup

distillationThe solvent was distilled off
customthe residue was purified by the silica gel column chromatography (volume ratio of chloroform:methanol=30:1)

Sources & evidence

ORD record: ord-66a2520e23df4c2595c7d3545e7e5550
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07396844B1

Reaction notes

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