1,3-Dihydroxy-1-(4-methylthio-phenyl)-2-ethoxycarbonylamino-propane → 5-(4-Methylthiophenyl)-4-hydroxymethyl-oxazolidin-2-one

HRID 5153Notes

Reaction equation

HRID 5153 reaction equation
O[CH:2]([C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)[CH:3]([NH:6][C:7]([O:9]CC)=[O:8])[CH2:4][OH:5]>C1(C)C=CC=CC=1>[CH3:19][S:18][C:15]1[CH:14]=[CH:13][C:12]([CH:2]2[O:9][C:7](=[O:8])[NH:6][CH:3]2[CH2:4][OH:5])=[CH:17][CH:16]=1

Participants

3

Reactant 1

HCID 136776181,3-Dihydroxy-1-(4-methylthio-phenyl)-2-ethoxycarbonylamino-propane

Product 1

HCID 136776195-(4-Methylthiophenyl)-4-hydroxymethyl-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Compound (H) (5 g; 17.5 mmols) has been dissolved in warm toluene (25 ml). To this solution, an equimolar amount of potassium tert. butylate has been added and the reaction mixture has been refluxed for 3 hours. Afterwards, almost all of the solvent has been evaporated; water and ice have been added to the residue and the precipitate has been collected by filtration. The thus obtained crude (J) has been recrystallized from ethanol (3.7 g; yield, 88%); m.p. 130°-131° C.

Workup

  1. temperaturethe reaction mixture has been refluxed for 3 hours
  2. customAfterwards, almost all of the solvent has been evaporated
  3. additionwater and ice have been added to the residue
  4. filtrationthe precipitate has been collected by filtration

Sources & evidence

ORD record
ord-235b5db98cd94164b1a080341731bb8b
Source dataset
uspto-grants-1993_09
Patent number
US05243056

Reaction notes

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