Pentanamide, N-[5-[[2-[2,4-bis(1,1-dimethylpropyl)phenoxy]-1-oxobutyl]amino]-2-chlorophenyl]-4,4-dimethyl-3-oxo- → HCID 4408645, compound

HRID 1379805Notes

Reaction equation

HRID 1379805 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:30])[CH:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([CH2:23][CH3:24])([CH3:22])[CH3:21])=[CH:16][C:15]=2[C:25]([CH2:28][CH3:29])([CH3:27])[CH3:26])[CH2:11][CH3:12])=[CH:4][C:3]=1[NH:31]C(=O)CC(=O)C(C)(C)C>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:30])[CH:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([CH2:23][CH3:24])([CH3:22])[CH3:21])=[CH:16][C:15]=2[C:25]([CH2:28][CH3:29])([CH3:27])[CH3:26])[CH2:11][CH3:12])=[CH:4][C:3]=1[NH2:31]

Participants

3

Reactant 1

HCID 119781Pentanamide, N-[5-[[2-[2,4-bis(1,1-dimethylpropyl)phenoxy]-1-oxobutyl]amino]-2-chlorophenyl]-4,4-dimethyl-3-oxo-

Product 1

HCID 4408645HCID 4408645, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Io 25 ml of ethyl acetate, was dispersed 5.71 g (0.01 mol) of N-[2-chloro-5-{2-(2,4-di-tert-amylphenoxy)butanoylamino}phenyl]-α-pivaloylacetic acid amide, which is easily obtained by a condensation reaction of 2-chloro-5-{2-(2,4-di-tert-amylphenoxy)butanoylamino}aniline with pivaloylacetic acid ester; and then to this was added, little by little, 1.57 g (0.0055 mol) of 1,3-dibromo-5,5-dimethylhydantoin, on an ice bath. After stirring for 1 hour, water was added to the resultant reaction mixture, followed by separation of solutions, and then a solvent was removed by fraction, to obtain on oily product. This product was subjected to silica gel column chromatography (n-hexane/ethyl acetate=10/1 to 5/1), for purification. As an oily product, 0.05 g of Compound (1)-1 was obtained.

Sources & evidence

ORD record
ord-28ec18cbdc764b86baba72781b38c2d3
Source dataset
uspto-grants-1997_09
Patent number
US05672714

Reaction notes

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