Water → Ethyl 6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]-3,3-dimethoxy-1-cyclohexene-1-carboxylate

HRID 546342Notes

Reaction equation

HRID 546342 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[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17]C(=O)[CH2:15][CH2:14]1)(=[O:12])=[O:11].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.CO[CH:44]([O:47][CH3:48])[O:45][CH3:46].O>CO>[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:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][C:44]([O:45][CH3:46])([O:47][CH3:48])[CH2:15][CH2:14]1)(=[O:11])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 9005Trimethyl orthoformateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57870910Ethyl 6-(N-(2-chloro-4-fluorophenyl)sulfamoyl)-3-oxocyclohex-1-ene-1-carboxylate

Product 1

HCID 67192731Ethyl 6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]-3,3-dimethoxy-1-cyclohexene-1-carboxylateYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6.1 g (16.2 mmol) of ethyl 6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]-3-oxo-1-cyclohexene-1-carboxylate obtained in Example 7 was dissolved in 120 ml of methanol and 4.1 g (16.2 mmol) of pyridinium p-toluenesulfonate and 8.86 ml (81.0 mmol) of trimethoxymethane were sequentially added thereto with stirring under ice-cooling, followed by stirring overnight at room temperature. Water was added to the reaction solution and the mixture was extracted with ethyl acetate. 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=2:1) to give 6.0 g of the title compound as a white powder (yield: 88%).

Workup

  1. temperaturecooling
  2. stirringby stirring overnight at room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationfollowed by concentration under reduced pressure

Sources & evidence

ORD record
ord-355088c366664774a6d630a856bfa91d
Source dataset
uspto-grants-2011_05
Patent number
US07935835B2

Reaction notes

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