Potassium Carbonate → (S)-N-{3-[4-(4-(Prop-2-yn-1-yl)-4-hydroxypiperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide

HRID 1026670Notes

Reaction equation

HRID 1026670 reaction equation
[Li][C:2]#[C:3][Si](C)(C)C.[O:8]=[C:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:25][C@H:24]([CH2:26][NH:27][C:28](=[O:30])[CH3:29])[O:23][C:22]3=[O:31])=[CH:17][C:16]=2[F:32])[CH2:11][CH2:10]1.[Cl-].[NH4+].[C:35](=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH2:35]([C:9]1([OH:8])[CH2:10][CH2:11][N:12]([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:25][C@H:24]([CH2:26][NH:27][C:28](=[O:30])[CH3:29])[O:23][C:22]3=[O:31])=[CH:17][C:16]=2[F:32])[CH2:13][CH2:14]1)[C:2]#[CH:3]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 54375226N-[(5S)-3-[3-fluoro-4-(4-oxopiperidinyl)phenyl]-2-oxo-5-oxazolidinyl]methylacetamideHCID 178506808HCID 178506808, compound

Product 1

HCID 11749595(S)-N-{3-[4-(4-(Prop-2-yn-1-yl)-4-hydroxypiperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamideYield 19%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
78 °C

Procedure

A mixture of lithio(trimethylsilyl)acetylene (1.72 mmol) and (S)—N-{3-[4-(4-oxo-piperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (1.72 mmol) in tetrahydrofuran (10 ml) was stirred at a temperature—78° C. for 15 minutes. It was allowed to come to room temperature and further stirred for 18 hours. The reaction mixture was then stirred with aqueous solution of ammonium chloride, the reaction mixture was extracted with ethyl acetate (3×40 ml). The removal of the solvent provided a residue, which was stirred in aqueous methanolic (15 ml) solution of potassium carbonate (1.72 mmol) for 3 hours. The solvent was removed and the residual mass was purified by column chromatography over silica gel to provide title compound in 19% yield. M.P. 166-167° C. and MS (M+1)=376 (MH+, 100%) M.F.=C19H22FN3O4.

Workup

  1. customto come to room temperature
  2. stirringfurther stirred for 18 hours
  3. extractionthe reaction mixture was extracted with ethyl acetate (3×40 ml)
  4. customThe removal of the solvent
  5. customprovided a residue, which
  6. customThe solvent was removed
  7. customthe residual mass was purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-247f63c77a014233bbc7514c526ed5ec
Source dataset
uspto-grants-2014_05
Patent number
US08729269B2

Reaction notes

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