HCID 53975389, compound → HCID 14459938, compound

HRID 892823Notes

Reaction equation

HRID 892823 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH:18]=[C:19]3[S:23][C:22](=[O:24])[NH:21][C:20]3=[O:25])=[CH:14][CH:13]=2)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[C:1]1([CH2:7][CH2:8][CH2:9][C:10]([C:12]2[CH:13]=[CH:14][C:15]([CH2:18][CH:19]3[S:23][C:22](=[O:24])[NH:21][C:20]3=[O:25])=[CH:16][CH:17]=2)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 53975389HCID 53975389, compoundHCID 131709961Jones' reagent

Product 1

HCID 14459938HCID 14459938, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of the title product of Example 66 (145 mg, 0.408 mmol) in acetone (10 ml) at 0° C. was added in a dropwise fashion Jones' Reagent (2.67M, 0.39 ml, 1.0 mmol). After stirring for 2 hours at room temperature, the reaction was quenched by the addition of isopropanol (1 ml) followed by water (20 ml), and stirred 10 minutes. The blue solution was decanted and extracted with EtOAc (2×20 ml). The combined organic layers were washed with water (20 ml), brine (20 ml), dried (MgSO4), filtered and concentrated to afford the present title product (129 mg, 90%); m.p. 120°-122° C.

Workup

  1. customthe reaction was quenched by the addition of isopropanol (1 ml)
  2. stirringstirred 10 minutes
  3. customThe blue solution was decanted
  4. extractionextracted with EtOAc (2×20 ml)
  5. washThe combined organic layers were washed with water (20 ml), brine (20 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7ae4c23348d2464fa09dae2e0c48b7d3
Source dataset
uspto-grants-1992_06
Patent number
US05120754

Reaction notes

Loading…