4-Toluenesulfonyl chloride → HCID 90283932, compound

HRID 336335Notes

Reaction equation

HRID 336335 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:7][O:6][C:5](=[O:8])[NH:4]1.[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1>ClCCl.CN(C)C1C=CN=CC=1>[CH3:19][C:9]1[CH:14]=[CH:13][C:12]([S:15]([O:1][CH2:2][C@H:3]2[CH2:7][O:6][C:5](=[O:8])[NH:4]2)(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 14456890(4S)-4-(hydroxymethyl)-1,3-oxazolidin-2-one

Product 1

HCID 90283932HCID 90283932, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of Intermediate 98 (11.0 g, 94.0 mmol) in dichloromethane (250 mL), 4-dimethylamino pyridine (22.94 g, 188.0 mmol) and p-toluene sulfonylchloride (26.88 g, 141.0 mmol) were added at 0° C. and it was stirred for an hour before bringing to the room temperature, and the reaction was stirred for an hour. The reaction mixture was washed with 1.5N hydrochloric acid (50 mL), water (50 mL), saturated sodium bicarbonate (50 mL) and finally with brine. The organic layer was dried over sodium sulfate and the solvent was removed under vacuum. The crude product was then purified by flash column chromatography in silica gel using a gradient of ethyl acetate in pet. ether. 1H NMR (300 MHz, DMSO-d6) δ: 2.49 (s, 3H), 3.91-3.95 (m, 2H), 3.99-4.02 (m, 2H), 4.30 (t, 1H), 7.49 (d, 2H), 7.80 (d, 2H), 7.88 (s, 1H). Yield: 12.0 g (47%).

Workup

  1. custombefore bringing to the room temperature
  2. stirringthe reaction was stirred for an hour
  3. washThe reaction mixture was washed with 1.5N hydrochloric acid (50 mL), water (50 mL), saturated sodium bicarbonate (50 mL) and finally with brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe solvent was removed under vacuum
  6. customThe crude product was then purified by flash column chromatography in silica gel using a gradient of ethyl acetate in pet. ether

Sources & evidence

ORD record
ord-e39e5f27c44e443d81d9ef6d1275043b
Source dataset
uspto-grants-2014_11
Patent number
US08889671B2

Reaction notes

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