Sodium Acetate → HCID 19754884, compound

HRID 1588911Notes

Reaction equation

HRID 1588911 reaction equation
[CH:1]1([N:7]([CH:30]([CH3:32])[CH3:31])[C:8](=[O:29])[C:9]2[CH:14]=[CH:13][C:12]([CH:15]([OH:28])[C:16]3[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=3)=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C([O-])(=O)C.[Na+]>C(Cl)Cl.C(OCC)C>[CH:1]1([N:7]([CH:30]([CH3:32])[CH3:31])[C:8](=[O:29])[C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:28])[C:16]3[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=3)=[CH:11][CH:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 19754877HCID 19754877, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 19754884HCID 19754884, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of the compound prepared in Example 14 (500 mg, 1.1 mmol) in CH2Cl2 (5 ml) was added to a stirred slurry of pyridinium chlorochromate (500 mg, 2.3 mmol) and sodium acetate (180 mg, 2.2 mmol) in CH2Cl2 (10 ml). The reaction was stirred for 2 hrs at room temperature and diluted with ethyl ether (50 ml). After stirring the mixture for 15 min., the mixture was filtered through Florisil® activated magnesium silicate (available from Aldrich Chemical Co., Milwaukee, Wisconsin, and the Florisil® was washed thoroughly with ether. The filtrate was concentrated in vacuo and the residue chromatographed over silica gel using mixtures of ethyl acetate and hexane as the eluents. The title compound was obtained pure as a glass.

Workup

  1. stirringAfter stirring the mixture for 15 min.
  2. filtrationthe mixture was filtered through Florisil® activated magnesium silicate (available from Aldrich Chemical Co
  3. wash, Milwaukee, Wisconsin, and the Florisil® was washed thoroughly with ether
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue chromatographed over silica gel using mixtures of ethyl acetate and hexane as the eluents

Sources & evidence

ORD record
ord-090f2bc795bf41d48fbee4e2c1ccea9f
Source dataset
uspto-grants-1993_06
Patent number
US05223539

Reaction notes

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