HCl tetrahydrofuran → Ethyl 6-(N-(2-chloro-4-fluorophenyl)sulfamoyl)-3-oxocyclohex-1-ene-1-carboxylate

HRID 546337Notes

Reaction equation

HRID 546337 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([CH:13]1[CH2:22][CH2:21][C:16]2(OCC[O:17]2)[CH:15]=[C:14]1[C:23]([O:25][CH2:26][CH3:27])=[O:24])(=[O:12])=[O:11].Cl.O1CCCC1>>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([CH:13]1[C:14]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:15][C:16](=[O:17])[CH2:21][CH2:22]1)(=[O:12])=[O:11]

Participants

3

Reactant 2

HCID 18422008HCl tetrahydrofuranHCID 57870947Ethyl 8-(N-(2-chloro-4-fluorophenyl)sulfamoyl)-1,4-dioxaspiro[4.5]dec-6-ene-7-carboxylate

Product 1

HCID 57870910Ethyl 6-(N-(2-chloro-4-fluorophenyl)sulfamoyl)-3-oxocyclohex-1-ene-1-carboxylateYield 96%

Procedure

To 2.55 g (6.07 mmol) of ethyl 8-[N-(2-chloro-4-fluorophenyl)sulfamoyl]-1,4-dioxaspiro[4.5]dec-6-ene-7-carboxylate obtained in Example 1 was added 100 ml of a mixed solution of 1N hydrochloric acid-tetrahydrofuran (1:1), and the reaction solution was stirred at room temperature for 64 hours. Tetrahydrofuran was distilled off under reduced pressure, the residue was extracted by addition of ethyl acetate, and the organic layer was washed with water and dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was subjected to silica gel column chromatography (solvent; hexane:ethyl acetate=4:1), to give 2.19 g of the title compound as a pale brown powder (yield: 96%).

Workup

  1. distillationTetrahydrofuran was distilled off under reduced pressure
  2. extractionthe residue was extracted by addition of ethyl acetate
  3. washthe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationfollowed by concentration under reduced pressure

Sources & evidence

ORD record
ord-566ccf61dcf040b085a40ac268a628af
Source dataset
uspto-grants-2011_05
Patent number
US07935835B2

Reaction notes

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