Nonanoyl chloride → 4-[4-(Nonanoylamino)-phenyl]-4-oxo-butyric acid

HRID 1168472Notes

Reaction equation

[C:1](Cl)(=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:26])[CH2:20][CH2:21][C:22]([O:24]C)=[O:23])=[CH:15][CH:14]=1>>[C:1]([NH:12][C:13]1[CH:14]=[CH:15][C:16]([C:19](=[O:26])[CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[CH:17][CH:18]=1)(=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

Reactant 2

HCID 69819Nonanoyl chloride

HCID 12016833Methyl 4-(4-aminophenyl)-4-oxobutanoate

Product 1

HCID 99021864-[4-(Nonanoylamino)-phenyl]-4-oxo-butyric acidYield 66%

Procedure

In a manner similar to that described in Example 3, nonanoyl chloride (0.055 g, 0.00031 mol) was allowed to react with 4-(4-amino-phenyl)-4-oxo-butyric acid, methyl ester (0.052 g, 0.00025 mol), and the resulting intermediate was hydrolyzed to give 0.055 g of 4-[4-(nonanoylamino)-phenyl]-4-oxo-butyric acid as an off-white solid; MS-(AP+) MH+334.

Sources & evidence

ORD record: ord-e02bce143ccb468ab88575a2676edee1
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06624196B2

Reaction notes

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