Ethyl Acetate → HCID 15622824, compound

HRID 327218Notes

Reaction equation

HRID 327218 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:17]2[C:18](=[O:27])[C:19]([CH3:26])=[C:20]([CH3:25])[C:21](=[O:24])[C:22]=2[CH3:23])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14](O)=[O:15])=[CH:4][CH:3]=1.Cl.[NH2:29][OH:30].C(=O)([O-])O.[Na+].C(OCC)(=O)C>ClCCl.C(Cl)(=O)C(Cl)=O.C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:17]2[C:18](=[O:27])[C:19]([CH3:26])=[C:20]([CH3:25])[C:21](=[O:24])[C:22]=2[CH3:23])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([NH:29][OH:30])=[O:15])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 15616468HCID 15616468, compound

Product 1

HCID 15622824HCID 15622824, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 65578Oxalyl chlorideSolvent

Conditions

Temperature
50 °C

Procedure

7-(4-Fluorophenyl)-7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-heptanoic acid (0.8 g, 2.2 mmol) was dissolved in dichloromethane (20 ml), to which oxalyl chloride (0.5 ml) was added at room temperature. The reaction mixture was stirred at 50° C. for 1 hour, and the solvent was evaporated under reduced pressure The resultant residue was dissolved in THF (5 ml), which was added dropwise at room temperature to a mixture of hydroxylamine hydrochloride (0.5 g, 7 mmol) in THF (10 ml) and saturated solution of aqueous sodium hydrogencarbonate (10 ml). After being stirred at room temperature for 1 hour, ethyl acetate (20 ml) was added to the reaction mixture. The organic layer was washed with water, dried, and concentrated under reduced pressure, and the resultant residue was recrystallized from isopropylether, to give 7-(4-fluorophenyl)-7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-heptanohydroxamic acid (0.7 g, 85%). The physical properties are shown in the column of Compound No.6 in Table 1. In the similar manner, Compounds Nos. 2, 3, 5, 7, 9, and 18 were synthesized.

Workup

  1. additionwas added at room temperature
  2. customthe solvent was evaporated under reduced pressure The resultant residue
  3. dissolutionwas dissolved in THF (5 ml)
  4. stirringAfter being stirred at room temperature for 1 hour
  5. washThe organic layer was washed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customthe resultant residue was recrystallized from isopropylether

Sources & evidence

ORD record
ord-086c3208b190458cbfaebfe3ba5c7834
Source dataset
uspto-grants-1993_12
Patent number
US05272180

Reaction notes

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