Hydroxyamine hydrochloride → (S)-N-{3-[3-fluoro-4-(4-hydroxyimino-piperidin-1-yl)-phenyl]-2-oxo oxazolidin-5-ylmethyl}-acetamide

HRID 1378692Notes

Reaction equation

HRID 1378692 reaction equation
C([O-])(=O)C.[Na+].Cl.[NH2:7][OH:8].[F:9][C:10]1[CH:11]=[C:12]([N:23]2[CH2:27][C@H:26]([CH2:28][NH:29][C:30](=[O:32])[CH3:31])[O:25][C:24]2=[O:33])[CH:13]=[CH:14][C:15]=1[N:16]1[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1>CO.C(Cl)Cl>[F:9][C:10]1[CH:11]=[C:12]([N:23]2[CH2:27][C@H:26]([CH2:28][NH:29][C:30](=[O:32])[CH3:31])[O:25][C:24]2=[O:33])[CH:13]=[CH:14][C:15]=1[N:16]1[CH2:21][CH2:20][C:19](=[N:7][OH:8])[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 54375226N-[(5S)-3-[3-fluoro-4-(4-oxopiperidinyl)phenyl]-2-oxo-5-oxazolidinyl]methylacetamide

Product 1

HCID 57115152(S)-N-{3-[3-fluoro-4-(4-hydroxyimino-piperidin-1-yl)-phenyl]-2-oxo oxazolidin-5-ylmethyl}-acetamideYield 82%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Sodium acetate (517 mg) and hydroxylamine hydrochloride (219 mg) were successively added to a methanol-methylene chloride solution (10-10 ml) of 1.00 g of the (S)-N-{3-[3-fluoro-4-(4-oxo-piperidin-1-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (Compound No. 7) synthesized in Example 3, and the mixture was stirred at room temperature for 2 days. The solvent was evaporated and the residue was dissolved in methanol, followed by addition of a silica gel (8 g). Methanol was evaporated and the residue was purified by silica gel column chromatography (solvent: chloroform/methanol=50/1-25/1) to afford the title compound (852 mg) in a yield of 82%.

Workup

  1. custom7) synthesized in Example 3
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in methanol
  4. additionfollowed by addition of a silica gel (8 g)
  5. customMethanol was evaporated
  6. customthe residue was purified by silica gel column chromatography (solvent: chloroform/methanol=50/1-25/1)

Sources & evidence

ORD record
ord-198f3850bd154d1faad9112974491897
Source dataset
uspto-grants-1997_09
Patent number
US05668286

Reaction notes

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