Octanoyl chloride → 4-[4-(Octanoylamino)-phenyl]-4-oxo-butyric acid

HRID 1264099Notes

Reaction equation

[C:1](Cl)(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:25])[CH2:19][CH2:20][C:21]([O:23]C)=[O:22])=[CH:14][CH:13]=1>>[C:1]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([C:18](=[O:25])[CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[CH:16][CH:17]=1)(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

Reactant 2

HCID 8124Octanoyl chloride

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

Product 1

HCID 103085844-[4-(Octanoylamino)-phenyl]-4-oxo-butyric acidYield 78.9%

Procedure

In a manner similar to that described in Example 3, octanoyl chloride (0.063 g, 0.00034 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 0.063 g of 4-[4-(octanoylamino)-phenyl]-4-oxo-butyric acid as an off-white solid; MS-(AP+) MH+320.

Sources & evidence

ORD record: ord-95879829c1b54490801b5eb6978ee12a
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06541521B1

Reaction notes

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