4-Toluenesulfonyl chloride → HCID 54120013, compound

HRID 1489447Notes

Reaction equation

HRID 1489447 reaction equation
[OH:1][C@@H:2]([C@H:7]([OH:15])[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)[C:3]([O:5][CH3:6])=[O:4].C(N(CC)CC)C.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>ClCCl>[F:14][C:11]1[CH:10]=[CH:9][C:8]([C@@H:7]([OH:15])[C@H:2]([O:1][S:29]([C:26]2[CH:27]=[CH:28][C:23]([CH3:33])=[CH:24][CH:25]=2)(=[O:31])=[O:30])[C:3]([O:5][CH3:6])=[O:4])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 53712574HCID 53712574, compound

Product 1

HCID 54120013HCID 54120013, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under argon atmosphere, a solution of methyl (2S,3R)-2,3-dihydroxy-3-(4-fluorophenyl)propionate (3.95 g, 18.4 mmol) dissolved in dichloromethane (100 ml) was cooled to -3° to -5° C., and triethylamine (3.86 ml, 27.7 mmol) and p-toluenesulfonyl chloride (3.62 g, 19.0 mmol) were added to the solution. After the mixture was stirred at -3° to -5° C. for 44 hours, the reaction mixture was washed with water and brine. After the organic layer was dried over anhydrous sodium sulfate, the solvent was removed, and the residue obtained was purified by silica gel flash column chromatography (ethyl acetate/hexane=1/2) to obtain methyl (2S,3R)-3-(4-fluorophenyl)-3-hydroxy-2-p-toluenesulfonyloxypropionate (5.64 g, yield: 83%).

Workup

  1. temperaturewas cooled to -3° to -5° C.
  2. washthe reaction mixture was washed with water and brine
  3. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was removed
  5. customthe residue obtained
  6. customwas purified by silica gel flash column chromatography (ethyl acetate/hexane=1/2)

Sources & evidence

ORD record
ord-bb2ba9d6de1140f99b45fa4231da1cc8
Source dataset
uspto-grants-1997_10
Patent number
US05677470

Reaction notes

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