Potassium Carbonate → HCID 67773564, compound

HRID 1963088Notes

Reaction equation

HRID 1963088 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[N:20]3[N:21]=[CH:22][C:23](C=O)=[CH:24][C:19]3=[C:18]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:17]=2[CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[C:35]=2[CH3:41])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:50])C=1.C(=O)([O-])O.[Na+].C(=O)([O-])[O-].[K+].[K+].S([O-])(O)(=O)=O.[K+]>C(Cl)Cl.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[N:20]3[N:21]=[CH:22][C:23]([OH:50])=[CH:24][C:19]3=[C:18]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:17]=2[CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[C:35]=2[CH3:41])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 516920Potassium bisulfateHCID 88414407HCID 88414407, compound

Product 1

HCID 67773564HCID 67773564, compoundYield 46.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the compound of step 2 (0.395 g, 0.71 mmol) in 7.1 ml of DCM was added 77% 3-chloro-perbenzoic acid (0.239 g, 1.06 mmol) in small portions and the solution was stirred at room temperature for 2.75 h. Then DCM (15 ml) and a saturated solution of sodium hydrogencarbonate (15 ml) were added and the aqueous phase was separated and extracted with DCM (15 ml). The combined organic phases were washed with brine (30 ml), dried over magnesium sulfate, filtered and evaporated to dryness under reduced pressure. The obtained oil was dissolved in 14 ml of MOH and stirred in the presence of potassium carbonate (0.147 g, 1.06 mmol) at room temperature for 15 min. Then water was added (15 ml) and the mixture was acidified to pH 5 by dropwise addition of a 1 M aqueous solution of potassium hydrogensulfate. The solution was then extracted twice with 15 ml each of EA and the combined organic phases were washed with brine (15 ml), dried over magnesium sulfate, filtered and evaporated to dryness. The residue was purified by chromatography on silica gel (DCM/EA, 80:20, then 60:40, then 40:60) to give 0.180 g of the title compound as a yellow solid melting at 165° C.

Workup

  1. customthe aqueous phase was separated
  2. extractionextracted with DCM (15 ml)
  3. washThe combined organic phases were washed with brine (30 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness under reduced pressure
  7. dissolutionThe obtained oil was dissolved in 14 ml of MOH
  8. extractionThe solution was then extracted twice with 15 ml each of EA
  9. washthe combined organic phases were washed with brine (15 ml)
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. customevaporated to dryness
  13. customThe residue was purified by chromatography on silica gel (DCM/EA, 80:20

Sources & evidence

ORD record
ord-00e5d7c396534d069ea41c6f3f3a1ca9
Source dataset
uspto-grants-2013_04
Patent number
US08415336B2

Reaction notes

Loading…