Water → (4-Methyl-2-oxooxazolidin-4-yl)methyl 4-methylbenzenesulfonate

HRID 539108Notes

Reaction equation

HRID 539108 reaction equation
[OH:1][CH2:2][C:3]1([CH3:9])[CH2:7][O:6][C:5](=[O:8])[NH:4]1.[S:10](Cl)([C:13]1[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=1)(=[O:12])=[O:11].O>N1C=CC=CC=1>[CH3:17][C:16]1[CH:18]=[CH:19][C:13]([S:10]([O:1][CH2:2][C:3]2([CH3:9])[CH2:7][O:6][C:5](=[O:8])[NH:4]2)(=[O:12])=[O:11])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 245546Nsc57599

Product 1

HCID 57461222(4-Methyl-2-oxooxazolidin-4-yl)methyl 4-methylbenzenesulfonateYield 86%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a chilled (0° C.) solution of 4-(hydroxymethyl)-4-methyloxazolidin-2-one (629 mg, 4.8 mmol) in anhydrous pyridine (4 ml) was added in portions tosyl chloride (1.05 g, 5.5 mmol). The solution was allowed to warm to ambient temperature and stirred under nitrogen for 48 hours. Water (12 mL) was added dropwise to the reaction mixture, and the resulting suspension was stirred at ambient temperature for 5 hours. The solids were isolated, and dried under vacuum to afford (4-methyl-2-oxooxazolidin-4-yl)methyl 4-methylbenzenesulfonate 1.17 g (86%).

Workup

  1. stirringthe resulting suspension was stirred at ambient temperature for 5 hours
  2. customThe solids were isolated
  3. customdried under vacuum

Sources & evidence

ORD record
ord-add157d696924a1b9f625d6d28d8d3d5
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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