Water → HCID 58398530, compound

HRID 1879415Notes

Reaction equation

HRID 1879415 reaction equation
O[CH:2]([CH3:34])[CH2:3][N:4]([S:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1)(=[O:27])=[O:26])[C:5]1[CH:22]=[C:21]([CH3:23])[C:20]([CH3:24])=[CH:19][C:6]=1[O:7][CH2:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1.C(N(S(F)(F)[F:41])CC)C.O>ClCCl>[F:41][CH:2]([CH3:34])[CH2:3][N:4]([S:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1)(=[O:27])=[O:26])[C:5]1[CH:22]=[C:21]([CH3:23])[C:20]([CH3:24])=[CH:19][C:6]=1[O:7][CH2:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 123472(Diethylamino)sulfur trifluorideHCID 58398406HCID 58398406, compound

Product 1

HCID 58398530HCID 58398530, compoundYield 23.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

460 mg of methyl 4-({2-[(2-hydroxypropyl)(pyridin-2-ylsulfonyl)amino]-4,5-dimethylphenoxy}methyl)benzoate was dissolved in 4.00 mL of dichloromethane, and 161 mg of diethylaminosulfur trifluoride was added dropwise thereto under ice-cooling, followed by stirring under ice-cooling for 30 minutes. To the reaction liquid was added water, followed by extraction with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1 to 1:1) to obtain 109 mg of methyl 4-({2-[(2-fluoropropyl)(pyridin-2-ylsulfonyl)amino]-4,5-dimethylphenoxy}methyl)benzoate.

Workup

  1. temperatureunder ice-cooling
  2. temperaturecooling for 30 minutes
  3. customTo the reaction liquid
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationThe solvent was concentrated under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1 to 1:1)

Sources & evidence

ORD record
ord-b7a68ba50ec2496b9218b9bfef5346f4
Source dataset
uspto-grants-2012_11
Patent number
US08314240B2

Reaction notes

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