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

HRID 2191149Notes

Reaction equation

HRID 2191149 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-f74b495b60f44a5aacbe4291e677565e
Source dataset
uspto-grants-2012_12
Patent number
USRE043858E1

Reaction notes

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