Potassium Carbonate → HCID 54350145, compound

HRID 1417466Notes

Reaction equation

HRID 1417466 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:20]=[CH:19][C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[C:9]=1[S:21][CH3:22].Br[CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26]>CC(C)=O>[CH3:22][S:21][C:9]1[C:10]2[NH:11][C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18]=2[CH:19]=[CH:20][C:8]=1[O:7][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 54416390HCID 54416390, compound

Product 1

HCID 54350145HCID 54350145, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

135 mg of powdered potassium carbonate was added to a solution of 112 mg of 2-hydroxy-1-methylthiocarbazole, as obtained in Example 2, in 4 ml of acetone. 956 mg of tert-butyl bromoacetate was added to the reaction mixture which was then stirred for 2 hours at room temperature. After this time, the reaction mixture was poured into ice water, and concentrated by evaporation under reduced pressure. The aqueous layer was extracted with ethyl acetate. The organic extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated by evaporation under reduced pressure. The resulting residue was subjected to column chromatography using 3 g of silica gel with a 9:1 v/v mixture of hexane and ethyl acetate as the eluent, to yield 140 mg of the title compound as an oil.

Workup

  1. concentrationconcentrated by evaporation under reduced pressure
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. additionwith a 9:1 v/v mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-236b461efe5244889a9e368951a4f79f
Source dataset
uspto-grants-1999_03
Patent number
US05877199

Reaction notes

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