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

HRID 495714Notes

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

Conditions

Temperature: 50 °C

Procedure

To a cooled (50° C.), stirred solution of (R)-1-(6-chloro-pyridin-3-yl)-ethane-1,2-diol (17.8 g) in anhydrous pyridine (100 mL) was added p-toluenesulfonyl chloride (19.5 g) in one portion. After 20 min, the cooling bath was removed and stirring was continued an additional 2 h. The reaction solution was concentrated in vacuo, azeotroped with toluene (2×), diluted in 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 23.3 g of the title compound (I-2d) as colorless crystals.

Workup

customthe cooling bath was removed
waitwas continued an additional 2 h
concentrationThe reaction solution was concentrated in vacuo
customazeotroped with toluene (2×)
additiondiluted in ethyl acetate
washwashed with half-saturated aqueous brine, saturated aqueous brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe resulting solids were recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record: ord-3c02a4c718c242b89cb96e686e2ce0f8
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06939867B2

Reaction notes

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