4-Toluenesulfonyl chloride → (R)-Toluene-4-sulfonic acid 2-(6-chloro-pyridin-3-yl)-2-hydroxy-ethyl ester

HRID 1059083Notes

Reaction equation

HRID 1059083 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C@@H:8]([OH:11])[CH2:9][OH:10])=[CH:4][CH:3]=1.[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1>N1C=CC=CC=1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C@@H:8]([OH:11])[CH2:9][O:10][S:18]([C:15]2[CH:16]=[CH:17][C:12]([CH3:22])=[CH:13][CH:14]=2)(=[O:20])=[O:19])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 11182911(r)-1-(6-Choro-pyridin-3-yl)-ethane-1,2-diol

Product 1

HCID 11738935(R)-Toluene-4-sulfonic acid 2-(6-chloro-pyridin-3-yl)-2-hydroxy-ethyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a cooled 5° C., stirred solution of (R)-1-(6-chloro-pyridin-3-yl)-ethane-1,2-diol (17.8 grams) in anhydrous pyridine (100 mL) was added p-toluenesulfonyl chloride (19.5 grams) in one portion. After 20 minutes, the cooling bath was removed and stirring was continued an additional 12 hours. The reaction solution was concentrated in vacuo, azeotroped with toluene (2 times), diluted ethyl acetate, washed with half-saturated aqueous brine, saturated aqueous brine, dried over sodium sulfate and concentrated in vacuo. The resulting solids were recrystallized from ethyl acetate/hexanes to afford the title compound as colorless crystals, 23.3 grams 1H NMR (400 MHz, CDCl3)=8.29 (s, 1H); 7.72 (d, 2H); 7.64 (d, 1H); 7.32 (d, 2H); 7.28 (d, 1H); 5.00 (dd, 1H); 4.09 (AB pattern, 2H); 2.44 (s, 3H).

Workup

  1. customthe cooling bath was removed
  2. waitwas continued an additional 12 hours
  3. concentrationThe reaction solution was concentrated in vacuo
  4. customazeotroped with toluene (2 times), diluted ethyl acetate
  5. washwashed with half-saturated aqueous brine, saturated aqueous brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe resulting solids were recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-634dd37b84934ece9903d3d9cb50e9db
Source dataset
uspto-grants-2003_02
Patent number
US06518431B2

Reaction notes

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