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

HRID 1105643
Notes
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Reaction equation

HRID 1105643 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 180AcetoneHCID 62365Isobutyl chloroformateHCID 459327Benzamide, N-(4-hydroxyphenyl)-HCID 3690897ACMC-20apjz

Product 1

HCID 571537857-(3-Hydroxy-5-oxo-1-cyclopenten-1-yl)-heptanoic acid p-benzoylaminophenyl ester

Reagents, catalysts & solvents 2

HCID 1049
Pyridine
Solvent
HCID 8471TriethylamineSolvent

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

  1. customAt -20° C.
  2. waitAfter 2 hours
  3. distillationthe solvent was distilled off
  4. extractionthe residue was extracted in ethyl acetate
  5. washthe organic phase was washed with water
  6. dry with materialdried over sodium sulphate
  7. distillationThe solvent was distilled off
  8. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes