Ethyl Acetate → HCID 23085071, compound

HRID 1727101Notes

Reaction equation

HRID 1727101 reaction equation
I([O-])(=O)(=O)=O.[Na+].[C:7]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][C:20]([CH2:24][S:25][C:26]3[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=3)([OH:23])[CH2:19][CH2:18]2)=[CH:11][CH:10]=1)#[N:8].C(=O)([O-])[O-:37].[K+].[K+].C(OCC)(=O)C>CO.O>[C:7]([C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][N:17]2[CH2:18][CH2:19][C:20]([CH2:24][S:25]([C:26]3[CH:27]=[CH:28][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:34][CH:35]=3)=[O:37])([OH:23])[CH2:21][CH2:22]2)=[CH:13][CH:14]=1)#[N:8]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 23085060HCID 23085060, compoundHCID 23667635Sodium periodate2×

Product 1

HCID 23085071HCID 23085071, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium metaperiodate (235 mg) was added to a solution of the compound (411 mg) obtained in Example 42 in a mixture of methanol (10 mL) and water (2 mL) under cooling with ice-water, followed by stirring at room temperature for one hour. Another portion of sodium metaperiodate (64 mg) was added, followed by stirring at room temperature for two hours. The reaction mixture was mixed with 10% aqueous potassium carbonate solution (10 mL) and ethyl acetate (20 mL), was stirred, and insoluble matter was removed by filtration. The filtrate was separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine and was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, the residue was purified by silica gel column chromatography [Chromatorex NH™] (eluent; hexane:ethyl acetate=3:1 to ethyl acetate) to yield the titled compound (180 mg) as crystals.

Workup

  1. stirringby stirring at room temperature for two hours
  2. stirringwas stirred
  3. custominsoluble matter was removed by filtration
  4. customThe filtrate was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washThe combined organic layer was washed with brine
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. customThe solvent was removed under reduced pressure
  9. customthe residue was purified by silica gel column chromatography [Chromatorex NH™] (eluent; hexane:ethyl acetate=3:1 to ethyl acetate)

Sources & evidence

ORD record
ord-6d1efcb458d046d0b8e181c337af0e21
Source dataset
uspto-grants-2009_02
Patent number
US07494987B2

Reaction notes

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