Acetone → 7-(3-Hydroxy-5-oxo-1-cyclopenten-1-yl)-heptanoic acid p-benzoylaminophenyl ester

HRID 1105643Notes

Reaction equation

[OH:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:3]1.CC(C)=O.ClC(OCC(C)C)=O.[C:29]([NH:37][C:38]1[CH:43]=[CH:42][C:41](O)=[CH:40][CH:39]=1)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>N1C=CC=CC=1.C(N(CC)CC)C>[C:29]([NH:37][C:38]1[CH:43]=[CH:42][C:41]([O:15][C:14](=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:4]2[C:5](=[O:7])[CH2:6][CH:2]([OH:1])[CH:3]=2)=[CH:40][CH:39]=1)(=[O:36])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

Conditions

Temperature: 25 °C

Procedure

0.326 g. of 7-(3-Hydroxy-5-oxo-1-cyclopenten-1-yl)-heptanoic acid were dissolved in 20 ml. of dry acetone. At -20° C., 0.23 ml. of triehtylamine were added and then 0.216 ml. isobutyl chloroformate. After 5 minutes, the temperature was permitted to increase to 25° C., and 0.4 g. of p-benzoylaminophenol dissolved in 10 ml. of dry pyridine was added dropwise. After 2 hours, the solvent was distilled off; the residue was extracted in ethyl acetate; the organic phase was washed with water and dried over sodium sulphate. The solvent was distilled off. After chromatographic purification of the residue (silica gel/ethyl acetate), 7-(3-hydroxy-5-oxo-1-cyclopenten-1-yl)-heptanoic acid p-benzoylaminophenyl ester (m.p. 168°-169° C.) was obtained.

Workup

customAt -20° C.
waitAfter 2 hours
distillationthe solvent was distilled off
extractionthe residue was extracted in ethyl acetate
washthe organic phase was washed with water
dry with materialdried over sodium sulphate
distillationThe solvent was distilled off
customAfter chromatographic purification of the residue (silica gel/ethyl acetate)

Sources & evidence

ORD record: ord-1f90fd7d2f6f452a9a05e11f7cf6d1af
Source dataset: uspto-grants-1982_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04309441

Reaction notes

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