Potassium Carbonate → HCID 68431530, compound

HRID 2246248Notes

Reaction equation

HRID 2246248 reaction equation
C(O[C:6]([NH:8][C@@H:9]([CH:18]([C:22]1[O:26][N:25]=[C:24]([C:27]2[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][C:28]=2[Cl:37])[N:23]=1)[CH2:19]C=C)[C:10]([N:12]1[CH2:16][CH2:15][C@H:14]([F:17])[CH2:13]1)=[O:11])=[O:7])(C)(C)C.[C:38](=O)([O-:40])[O-:39].[K+].[K+].I([O-])(=O)(=O)=O.[Na+].[Mn]([O-])(=O)(=O)=O.[K+].[C:56]([OH:60])([CH3:59])([CH3:58])[CH3:57].O>>[C:56]([O:60][C:6]([NH:8][C@H:9]([C:10]([N:12]1[CH2:16][CH2:15][C@H:14]([F:17])[CH2:13]1)=[O:11])[CH:18]([C:22]1[O:26][N:25]=[C:24]([C:27]2[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:34])=[O:35])=[CH:29][C:28]=2[Cl:37])[N:23]=1)[CH2:19][C:38]([OH:40])=[O:39])=[O:7])([CH3:59])([CH3:58])[CH3:57]

Participants

6

Reactant 5

HCID 11430Potassium CarbonateHCID 516875Potassium PermanganateHCID 23667635Sodium periodateHCID 68431247HCID 68431247, compoundHCID 714019492-Methylpropan-2-ol--water (1/1)

Product 1

HCID 68431530HCID 68431530, compound

Procedure

To the product of Step A (221 mg, 0.4 mmol) in 50 mL of 4:1 tert-butanol/water was added potassium carbonate (69 mg, 0.4 mmol), sodium periodate (870 mg, 4.0 mmol), and potassium permanganate (8 mg, 0.05 mmol) and the resulting pink slurry was stirred at room temperature for 12 h. The mixture was then quenched with 10 mL of saturated aqueous sodium bisulfite solution then diluted with 80 mL of 1N hydrochloric acid. The mixture was then extracted with ethyl acetate (3×75 mL), and the organic layers were washed sequentially with 1N hydrochloric acid and saturated aqueous brine (2×50 mL each). The organic phase was dried over magnesium sulfate, filtered, and evaporated in vacuo to yield the crude acid, which was used without further purification. LC/MS 575.3 (M+1), 577.2 (M+3).

Workup

  1. customThe mixture was then quenched with 10 mL of saturated aqueous sodium bisulfite solution
  2. additionthen diluted with 80 mL of 1N hydrochloric acid
  3. extractionThe mixture was then extracted with ethyl acetate (3×75 mL)
  4. washthe organic layers were washed sequentially with 1N hydrochloric acid and saturated aqueous brine (2×50 mL each)
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-405bada6ead44723a7aeaa29f309b232
Source dataset
uspto-grants-2010_03
Patent number
US07687492B2

Reaction notes

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