4-Toluenesulfonyl chloride → HCID 54390514, compound

HRID 1489450Notes

Reaction equation

HRID 1489450 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@H:9]([OH:16])[C@H:10]([OH:15])[C:11]([O:13][CH3:14])=[O:12].[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.C(N(CC)CC)C>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@H:9]([OH:16])[C@H:10]([O:15][S:23]([C:20]1[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=1)(=[O:25])=[O:24])[C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 54409187HCID 54409187, compound

Product 1

HCID 54390514HCID 54390514, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Under argon atmosphere, a solution of 955 mg of methyl (2S,3R)-3-(2,4-difluorophenyl)-2,3-dihydroxypropionate dissolved in 30 ml of dichloromethane was cooled to 0° C., and to the solution was added 940 mg of p-toluenesulfonyl chloride and 624 mg of triethylamine. After the mixture was stirred at 0° C. for 3 days, the reaction mixture was washed with water and dried, and the solvent was removed. The residue was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=2:1) to obtain 1.15 g of methyl (2S,3R)-3-(2,4-difluorophenyl)-3-hydroxy-2-(p-toluenesulfonyloxy)propionate.

Workup

  1. washthe reaction mixture was washed with water
  2. customdried
  3. customthe solvent was removed
  4. customThe residue was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-23e2c6b05c344ae6a177685d8dbbee4c
Source dataset
uspto-grants-1997_10
Patent number
US05677470

Reaction notes

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