Water → HCID 86627546, compound

HRID 1970043Notes

Reaction equation

HRID 1970043 reaction equation
[OH:1]OS([O-])=O.[K+].[CH:7]1([S:13][C:14]2[CH:23]=[CH:22][C:21]3[NH:20][C:19](=[O:24])[C:18]4[NH:25][CH:26]=[CH:27][C:17]=4[C:16]=3[CH:15]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[CH2:28]([C:30]([O-:32])=[O:31])[CH3:29].[OH2:33]>CO.C(#N)C>[CH:7]1([S:13]([C:14]2[CH:23]=[CH:22][C:21]3[NH:20][C:19](=[O:24])[C:18]4[NH:25][CH:26]=[CH:27][C:17]=4[C:16]=3[CH:15]=2)(=[O:1])=[O:33])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1.[CH2:28]([C:30]([O-:32])=[O:31])[CH3:29]

Participants

6

Reactant 3

HCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 86627547HCID 86627547, compound

Product 1

HCID 86627546HCID 86627546, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 410 mg (0.66 mmol) of Oxone in 2 mL of water is added to a solution of 49 mg (0.13 mmol) of 8-cyclohexylsulfanyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in methanol (5 mL) and acetonitrile (1 mL). The solution is stirred at room temperature for 24 hours. The solvents are evaporated then the residue is taken up in water. The product is extracted with ethyl acetate and the organic phases are dried over magnesium sulfate, filtered and evaporated. The residue is triturated in diethyl ether to give 40 mg (74%) of 8-cyclohexanesulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a white solid.

Workup

  1. customThe solvents are evaporated
  2. extractionThe product is extracted with ethyl acetate
  3. dry with materialthe organic phases are dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is triturated in diethyl ether

Sources & evidence

ORD record
ord-59b361ff34104b2c80986890d86772d3
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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