Benzene → HCID 86751255, compound

HRID 1378696Notes

Reaction equation

HRID 1378696 reaction equation
[N:1]#[C:2][NH2:3].[F:4][C:5]1[CH:6]=[C:7]([N:18]2[CH2:22][C@H:21]([CH2:23][NH:24][C:25](=[O:27])[CH3:26])[O:20][C:19]2=[O:28])[CH:8]=[CH:9][C:10]=1[N:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1.C1C=CC=CC=1>O>[C:2]([N:3]=[C:14]1[CH2:15][CH2:16][N:11]([C:10]2[CH:9]=[CH:8][C:7]([N:18]3[CH2:22][C@H:21]([CH2:23][NH:24][C:25](=[O:27])[CH3:26])[O:20][C:19]3=[O:28])=[CH:6][C:5]=2[F:4])[CH2:12][CH2:13]1)#[N:1]

Participants

5

Reactant 3

HCID 241BenzeneHCID 9864CyanamideHCID 54375226N-[(5S)-3-[3-fluoro-4-(4-oxopiperidinyl)phenyl]-2-oxo-5-oxazolidinyl]methylacetamide

Product 1

HCID 86751255HCID 86751255, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Cyanamide (601 mg) and 500 mg of the (S)-N-{3-[3-fluoro-4-(4-oxo-piperidin-1-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (Compound No. 7) which was synthesized in Example 3 were added to benzene (70 ml), and the mixture was heated under reflux for 2 h, with water being removed continuously by means of a water separator. The reaction mixture was cooled to room temperature and the resulting crystal was collected by filtration. After being washed with water, the crystal was dried overnight at 40° C. under vacuum to afford the title compound (423 mg) in a yield of 79%.

Workup

  1. custom7) which was synthesized in Example 3
  2. temperaturethe mixture was heated
  3. customremoved continuously by means of a water separator
  4. filtrationthe resulting crystal was collected by filtration
  5. washAfter being washed with water
  6. customthe crystal was dried overnight at 40° C. under vacuum

Sources & evidence

ORD record
ord-a06f542abd394008a279f394c114f2bd
Source dataset
uspto-grants-1997_09
Patent number
US05668286

Reaction notes

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