HCID 17866489, compound → HCID 17866590, compound

HRID 583379Notes

Reaction equation

HRID 583379 reaction equation
[CH2:1]([N:8]([C:20]1[C:25]([CH3:26])=[CH:24][CH:23]=[C:22]([CH3:27])[C:21]=1[CH2:28][OH:29])[S:9]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH2:1]([N:8]([C:20]1[C:25]([CH3:26])=[CH:24][CH:23]=[C:22]([CH3:27])[C:21]=1[CH:28]=[O:29])[S:9]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 17866489HCID 17866489, compoundHCID 131709961Jones' reagent

Product 1

HCID 17866590HCID 17866590, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 438.7 mg of the product of Example 289 in 20 ml of acetone was added 5.33 ml (10.07 mmol) of Jones reagent and the reaction was stirred at room temperature for 18 hr. The resulting mixture was concentrated in vacuo and the residue was diluted with dichloromethane, washed with water and brine, dried over MgSO4, filtered and concnentrated in vacuo. The residue was triturated with hexane to provide 396 mg (91%) of the desired product as a white solid. Electrospray Mass Spec 410 (M+H).

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. additionthe residue was diluted with dichloromethane
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe residue was triturated with hexane

Sources & evidence

ORD record
ord-30b4c19e305a4aacb9feffbf34ca0664
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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