Heptanoyl chloride → 4-[4-(Heptanoylamino)-phenyl]-4-oxo-butyric acid

HRID 1168475Notes

Reaction equation

[C:1](Cl)(=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:24])[CH2:18][CH2:19][C:20]([O:22]C)=[O:21])=[CH:13][CH:12]=1>>[C:1]([NH:10][C:11]1[CH:12]=[CH:13][C:14]([C:17](=[O:24])[CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:15][CH:16]=1)(=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

Reactant 2

HCID 17313Heptanoyl chloride

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

Product 1

HCID 99225304-[4-(Heptanoylamino)-phenyl]-4-oxo-butyric acidYield 62.9%

Procedure

In a manner similar to that described in Example 3, heptanoyl chloride (0.051 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 0.048 g of 4-[4-(heptanoylamino)-phenyl]-4-oxo-butyric acid as an off-white solid; MS-(AP+) MH+306.

Sources & evidence

ORD record: ord-a3906be9cf144e5fa1f14dc1e23875e0
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06624196B2

Reaction notes

Loading…