Water → 3,5-Dioxohexanoic acid

HRID 1736328Notes

Reaction equation

HRID 1736328 reaction equation
CC(C)=CCC/C(/C)=C/CC/C(/C)=C/CN1C(=O)C2C=CC=C(O)C=2N[C:19]2[C:18]([OH:30])=[CH:17][C:16]([OH:31])=CC1=2.C([O:38][C:39](=[O:41])[CH3:40])(=O)C.CCOC(C)=O.O>N1C=CC=CC=1>[CH3:19][C:18]([CH2:17][C:16]([CH2:40][C:39]([OH:38])=[O:41])=[O:31])=[O:30]

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 9868980Diazepinomicin

Product 1

HCID 54598443,5-Dioxohexanoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

BU-4664L (20 rag) was stirred with acetic anhydride (1.0 ml) in anhydrous pyridine (1.5 ml) for 18 hours at room temperature. To the reaction mixture, EtOAc and water (20 ml each) were added and stirred for one hour. After washing with water (20 ml portions) twice, the organic layer was concentrated to give a yellow solid. The residue was purified by preparative TLC (SiO2, CH2Cl2 -MeOH 20:1) followed by Sephadex LH-20 chromatography using CH2Cl2 -MeOH (4:6) as a developing solvent to give triacetate BU-4664L (2, 13 mg), m.p. >200° C. (dec.).

Workup

  1. washAfter washing with water (20 ml portions) twice
  2. concentrationthe organic layer was concentrated
  3. customto give a yellow solid
  4. customThe residue was purified by preparative TLC (SiO2, CH2Cl2 -MeOH 20:1)

Sources & evidence

ORD record
ord-e0ac8b2d1aa54a13afe8a8ad5d2082a7
Source dataset
uspto-grants-1996_07
Patent number
US05541181

Reaction notes

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