Water → HCID 22261642, compound

HRID 1610665Notes

Reaction equation

HRID 1610665 reaction equation
[Cl:1][C:2]1[S:6][C:5]([CH:7]2[O:11]C(=O)[NH:9][CH:8]2[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]([F:26])([F:25])[CH:22]([F:24])[F:23])[CH:15]=2)=[CH:4][CH:3]=1.[OH-].[Na+].O>C(O)C.[Cl-].[Na+].O>[NH2:9][CH:8]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]([F:25])([F:26])[CH:22]([F:23])[F:24])[CH:15]=1)[CH:7]([C:5]1[S:6][C:2]([Cl:1])=[CH:3][CH:4]=1)[OH:11]

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 22261382HCID 22261382, compound

Product 1

HCID 22261642HCID 22261642, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

(4RS,5RS)-5-(5-Chloro-2-thienyl)-4-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]-1,3-oxazolidin-2-one (8.480 g, 20.69 mmol) and sodium hydroxide (3.31 g, 82.8 mmol) were heated in ethanol (40 ml)-water (3 ml) under reflux for 4 hrs. The reaction solution was diluted with brine, and extracted twice with ethyl acetate. The recovered organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel (APS type) column chromatography (hexane/ethyl acetate=3/1-ethyl acetate) to give the objective substance.

Workup

  1. temperatureunder reflux for 4 hrs
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe recovered organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel (APS type) column chromatography (hexane/ethyl acetate=3/1-ethyl acetate)
  6. customto give the objective substance

Sources & evidence

ORD record
ord-21403f0f28ea431b9f7613df21418304
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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