Acetone → N-[(5S)-3-[3-fluoro-4-(4-oxopiperidinyl)phenyl]-2-oxo-5-oxazolidinyl]methylacetamide

HRID 609576Notes

Reaction equation

HRID 609576 reaction equation
O=C1C2(CCNCC2)C(=O)CC1.O1[C:17]2([CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][C:26]([N:29]4[CH2:33][C@H:32]([CH2:34][NH:35][C:36](=[O:38])[CH3:37])[O:31][C:30]4=[O:39])=[CH:25][C:24]=3[F:40])[CH2:19][CH2:18]2)[O:16]CC1.CC(C)=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[F:40][C:24]1[CH:25]=[C:26]([N:29]2[CH2:33][C@H:32]([CH2:34][NH:35][C:36](=[O:38])[CH3:37])[O:31][C:30]2=[O:39])[CH:27]=[CH:28][C:23]=1[N:20]1[CH2:21][CH2:22][C:17](=[O:16])[CH2:18][CH2:19]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 2880631,4-Dioxo-8-azaspiro[4,5]decaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 9952477(S)-N-{3-[4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide

Product 1

HCID 54375226N-[(5S)-3-[3-fluoro-4-(4-oxopiperidinyl)phenyl]-2-oxo-5-oxazolidinyl]methylacetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Using a commercially available 1,4-dioxo-8-aza-spiro[4.5]decane, (S)-N-{3-[4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmethyl}- acetamide is synthesized by the same method as in Step 1. To an acetone solution (70 ml) of this compound (3.79 g), water (20 ml) and p-toluenesulfonic acid monohydrate (3.66 g) are added successively and the mixture is heated under reflux for 3 hours. After the reaction mixture is cooled to room temperature, acetone is distilled off and the aqueous layer is neutralized with triethylamine. The solution is extracted with methylene chloride and the organic layer is washed with brine, dried over anhydrous sodium sulfate. The solvent is evaporated and the residue is purified by silica gel column chromatography (solvent: chloroform/methanol=50/1-25/1) to afford the title compound.

Workup

  1. customis synthesized by the same method as in Step 1
  2. temperaturethe mixture is heated
  3. temperatureunder reflux for 3 hours
  4. distillationacetone is distilled off
  5. extractionThe solution is extracted with methylene chloride
  6. washthe organic layer is washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent is evaporated
  9. customthe residue is purified by silica gel column chromatography (solvent: chloroform/methanol=50/1-25/1)

Sources & evidence

ORD record
ord-e8657d2588d64e309c6250919b260b10
Source dataset
uspto-grants-1999_12
Patent number
US05998406

Reaction notes

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