Ammonium Acetate → (S)-N-{3-[4-(4-(1-Cyano-cyclopropylmethylidene)-piperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide

HRID 750932

Reaction equation

HRID 750932 reaction equation
O=C1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][NH:20][C:21](=[O:23])[CH3:22])[O:16][C:15]3=[O:24])=[CH:10][C:9]=2[F:25])[CH2:4][CH2:3]1.[CH:26]1([CH2:29][C:30]#N)[CH2:28][CH2:27]1.[C:32]([O-])(=O)C.[NH4+:36]>C1(C)C=CC=CC=1>[C:32]([C:26]1([CH:29]=[C:30]2[CH2:7][CH2:6][N:5]([C:8]3[CH:13]=[CH:12][C:11]([N:14]4[CH2:18][C@H:17]([CH2:19][NH:20][C:21](=[O:23])[CH3:22])[O:16][C:15]4=[O:24])=[CH:10][C:9]=3[F:25])[CH2:4][CH2:3]2)[CH2:27][CH2:28]1)#[N:36]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 643447CyclopropylacetonitrileHCID 54375226N-[(5S)-3-[3-fluoro-4-(4-oxopiperidinyl)phenyl]-2-oxo-5-oxazolidinyl]methylacetamide

Product 1

HCID 69312101(S)-N-{3-[4-(4-(1-Cyano-cyclopropylmethylidene)-piperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamideYield 69%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The mixture of (S)-N-{3-[4-(4-oxo-piperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (2.86 mmol), cyclopropylacetonitrile (5.73 mmol), ammonium acetate (catalytic) in 100 ml of toluene was heated at reflux temperature for 5 to 6 hours. The reaction mixture was cooled to room temperature and extracted with ethyl acetate water mixture, dried and evaporated to give crude product. The crude product was recrystallized from ethyl acetate to furnish title compound in 69% yield.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 5 to 6 hours
  3. extractionextracted with ethyl acetate water mixture
  4. customdried
  5. customevaporated
  6. customto give crude product
  7. customThe crude product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9afbb5837de94abc90f0dfb3b34b7efb
Source dataset
uspto-grants-2008_07
Patent number
US07405228B2

Linked notes

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