Hydrazine → N-[[(5S)-3-[3-fluoro-4-(hydrazinecarbonyl)phenyl]-2-oxo-oxazolidin-5-yl]methyl]acetamide

HRID 351880Notes

Reaction equation

HRID 351880 reaction equation
[NH2:1][NH2:2].[C:3]([NH:6][CH2:7][C@@H:8]1[O:12][C:11](=[O:13])[N:10]([C:14]2[CH:19]=[CH:18][C:17]([C:20](OC3C(F)=C(F)C(F)=C(F)C=3F)=[O:21])=[C:16]([F:34])[CH:15]=2)[CH2:9]1)(=[O:5])[CH3:4]>O1CCCC1>[C:3]([NH:6][CH2:7][C@@H:8]1[O:12][C:11](=[O:13])[N:10]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([NH:1][NH2:2])=[O:21])=[C:16]([F:34])[CH:15]=2)[CH2:9]1)(=[O:5])[CH3:4]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 229661965-(S)-acetamidomethyl-3-[4'-(pentafluorophenoxy)carbonyl-3'-fluorophenyl]oxazolidine-2-one

Product 1

HCID 485756N-[[(5S)-3-[3-fluoro-4-(hydrazinecarbonyl)phenyl]-2-oxo-oxazolidin-5-yl]methyl]acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Hydrazine (0.041 ml, 1.30 mmol) was added dropwise with stirring to a solution of 5-(S)-acetamidomethyl-3-[4′-(pentafluorophenoxy)carbonyl-3′-fluorophenyl]oxazolidine-2-one (0.500 g, 1.08 mmol) in tetrahydrofuran (3 ml). The mixture was stirred at r.t. for 2 h, and the heavy white precipitate filtered, washed with ether, and dried under vacuum. Yield 0.295 g (88%). MS (m/z): [M+H]+=311.

Workup

  1. filtrationthe heavy white precipitate filtered
  2. washwashed with ether
  3. customdried under vacuum

Sources & evidence

ORD record
ord-255d22e9b93c470fbc5736d323abb462
Source dataset
uspto-grants-2004_06
Patent number
US06743811B2

Reaction notes

Loading…