Water → HCID 131726953, compound

HRID 747493Notes

Reaction equation

HRID 747493 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[C@@H:14]([CH2:15][CH2:16][OH:17])[O:13][CH2:12][CH2:11][N:10]2[C:18](=[O:33])[C:19]2[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([C:29]([F:32])([F:31])[F:30])[CH:20]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(CC)CC)C.[CH3:41][S:42](Cl)(=[O:44])=[O:43].O>C(Cl)Cl>[CH3:41][S:42]([O:17][CH2:16][CH2:15][C@H:14]1[O:13][CH2:12][CH2:11][N:10]([C:18](=[O:33])[C:19]2[CH:20]=[C:21]([C:29]([F:30])([F:31])[F:32])[CH:22]=[C:23]([C:25]([F:26])([F:27])[F:28])[CH:24]=2)[CH:9]1[C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)(=[O:44])=[O:43]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 131726954HCID 131726954, compound

Product 1

HCID 131726953HCID 131726953, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.68 g (11 mmol) of the resulting alcohol derivative were dissolved in methylene chloride (60 ml) followed by the addition of 2.3 ml (16.5 mmol) of triethylamine under a nitrogen atmosphere, the addition of 1.02 ml (13.2 mmol) of methanesulfonyl chloride with ice-cooling, and stirring for 30 minutes at room temperature under a nitrogen atmosphere. Water was then added to the reaction solution followed by washing the methylene chloride layer with water and a saturated aqueous solution of sodium chloride and drying with anhydrous magnesium sulfate. After filtering, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=3/2) to obtain 6.09 g of the desired compound (93%).

Workup

  1. temperaturecooling
  2. washby washing the methylene chloride layer with water
  3. dry with materiala saturated aqueous solution of sodium chloride and drying with anhydrous magnesium sulfate
  4. filtrationAfter filtering
  5. distillationthe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=3/2)

Sources & evidence

ORD record
ord-499d2b9beb5c423295c9da9febc7ca90
Source dataset
uspto-grants-2008_07
Patent number
US07396930B2

Reaction notes

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