Dimethylformamide dimethyl acetal → HCID 53769776, compound

HRID 1378697Notes

Reaction equation

HRID 1378697 reaction equation
CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[NH2:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:26][C@H:25]([CH2:27][NH:28][C:29](=[O:31])[CH3:30])[O:24][C:23]3=[O:32])=[CH:18][C:17]=2[F:33])[CH2:12][CH2:11]1>C1(C)C=CC=CC=1>[CH3:3][N:4]([CH:6]=[N:9][CH:10]1[CH2:11][CH2:12][N:13]([C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:26][C@H:25]([CH2:27][NH:28][C:29](=[O:31])[CH3:30])[O:24][C:23]3=[O:32])=[CH:18][C:17]=2[F:33])[CH2:14][CH2:15]1)[CH3:5]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 54437918HCID 54437918, compound

Product 1

HCID 53769776HCID 53769776, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N,N-dimethylformamide dimethylacetal (0.8 ml) and 1.0 g of the (S)-N-{3-[4-(4-amino-piperidin-1-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (Compound No. 6) which was synthesized in Example 4 were added to toluene (10 ml) and the mixture was heated under reflux for 24 h. The reaction mixture was cooled to room temperature and concentrated under vacuum. The residue was washed with hexane to remove excess dimethylacetal. The resulting precipitate was suspended in dichloromethane and the insolubles were separated by filtration. The filtrate was concentrated under vacuum to afford the title compound (985 mg) in a yield of 84%.

Workup

  1. custom6) which was synthesized in Example 4
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 24 h
  4. concentrationconcentrated under vacuum
  5. washThe residue was washed with hexane
  6. customto remove excess dimethylacetal
  7. customthe insolubles were separated by filtration
  8. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-ce9a38af2f3f4e1ea9bee9eb45181b5e
Source dataset
uspto-grants-1997_09
Patent number
US05668286

Reaction notes

Loading…