4,7-Dioxo-7-phenylheptanoic acid → HCID 67223722, compound

HRID 2359983Notes

Reaction equation

O=[C:2]([CH2:8][CH2:9][C:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[NH2:18][C:19]1[CH:31]=[CH:30][C:22]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:21][CH:20]=1>C(O)(=O)C>[C:26]([O:25][C:23](=[O:24])[C:22]1[CH:21]=[CH:20][C:19]([N:18]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][CH:8]=[C:2]2[CH2:3][CH2:4][C:5]([OH:7])=[O:6])=[CH:31][CH:30]=1)([CH3:29])([CH3:27])[CH3:28]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 4,7-dioxo-7-phenyl-heptanoic acid (3.57 mmol, 1.0 eq.) in acetic acid (10 ml) was added tert-butyl 4-aminobenzoate (1.05 eq., 3.75 mmol). The mixture was heated to 80° C. for 36 hours. The solvent was evaporated in vacuo and the crude residue purified by flash silica-gel chromatography. Gradient elution with ethyl acetate/hexane (0% to 50% ethyl acetate in hexane over 20 minutes) gave the semi-pure product after combination of the appropriate fractions and evaporation of the solvent in vacuo. The tan solid obtained was used without further purification, 59% yield.

Workup

customThe solvent was evaporated in vacuo
customthe crude residue purified by flash silica-gel chromatography
washGradient elution with ethyl acetate/hexane (0% to 50% ethyl acetate in hexane over 20 minutes)
customgave the semi-pure product
customafter combination of the appropriate fractions and evaporation of the solvent in vacuo
customThe tan solid obtained
customwas used without further purification, 59% yield

Sources & evidence

ORD record: ord-f45955f7226e4a6b8f2b7f7eed5b4c30
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08686015B2

Reaction notes

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