Triethylamine → HCID 69921162, compound

HRID 2414426Notes

Reaction equation

HRID 2414426 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]([O:37][CH2:38][CH3:39])(=[O:36])[CH:34]=[CH2:35].C(N(CC)CC)C.C(OCC)(=O)C>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([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])[CH2:22][O:23][C:24]1[CH:29]=[C:28]([C:30]#[N:31])[CH:27]=[CH:26][C:25]=1[CH:35]=[CH:34][C:33]([O:37][CH2:38][CH3:39])=[O:36])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 8857Ethyl AcetateHCID 86584116HCID 86584116, compound

Product 1

HCID 69921162HCID 69921162, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

1.64 g (2.98 mmol) of benzyl (4S)-4-t-butoxycarbonylamino-5-(5-cyano-2-iodophenoxy)pentanoate was dissolved in 30 ml of N,N-dimethylformamide (dehydrated). 0.65 ml (5.96 mmol) of ethyl acrylate, 2.1 ml (14.9 mmol) of triethylamine and 14 mg (0.06 mmol) of palladium acetate were added to the obtained solution, and they were stirred at 100° C. overnight. After the treatment with ethyl acetate as the extraction solvent in an ordinary manner, the obtained crude product was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. customwas purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-f584de1f6b064b7a92332614fa168c7b
Source dataset
uspto-grants-2004_11
Patent number
US06812231B2

Reaction notes

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