Potassium Carbonate → HCID 86627548, compound

HRID 1970044Notes

Reaction equation

HRID 1970044 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([S:19][C:20]1[CH:29]=[CH:28][C:27]2[NH:26][C:25](=[O:30])[C:24]3[NH:31][CH:32]=[CH:33][C:23]=3[C:22]=2[CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH2:34]([C:36]([O-:38])=[O:37])[CH3:35].C(=O)([O-])[O-].[K+].[K+]>ClCCl.O1CCOCC1>[O:30]=[C:25]1[C:24]2[NH:31][CH:32]=[CH:33][C:23]=2[C:22]2[CH:21]=[C:20]([S:19]([CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[O:9])[CH:29]=[CH:28][C:27]=2[NH:26]1.[CH2:34]([C:36]([O-:38])=[O:37])[CH3:35]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 86627549HCID 86627549, compound

Product 1

HCID 86627548HCID 86627548, compoundYield 42.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
2.5 °C

Procedure

41 mg (0.24 mmol) of metachloroperbenzoic acid is added at 0° C. to a solution of 90 mg (0.24 mmol) of 8-benzylsulfanyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate suspended in dichloromethane (8 mL) and dioxan (8 mL). The reaction mixture is stirred for 6 hours at 0-5° C. then an aqueous solution of potassium carbonate is added and the product is extracted with ethyl acetate. The organic phase is washed with an aqueous solution of sodium chloride, dried over magnesium sulfate, filtered and evaporated. The residue is purified by preparative LCMS to give 40 mg (42%) of 4-oxo-8-phenylmethanesulfinyl-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a white solid.

Workup

  1. extractionthe product is extracted with ethyl acetate
  2. washThe organic phase is washed with an aqueous solution of sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is purified by preparative LCMS

Sources & evidence

ORD record
ord-4fd4835aa53d455397c8fc6a3fba1d32
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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