Nitromethane → (S)-N-{3-[4-(4-Nitromethyl-4-hydroxypiperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide

HRID 1026677Notes

Reaction equation

HRID 1026677 reaction equation
[H-].[Na+].[N+:3]([CH3:6])([O-:5])=[O:4].[O:7]=[C:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][NH:26][C:27](=[O:29])[CH3:28])[O:22][C:21]3=[O:30])=[CH:16][C:15]=2[F:31])[CH2:10][CH2:9]1>O1CCCC1>[N+:3]([CH2:6][C:8]1([OH:7])[CH2:9][CH2:10][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][NH:26][C:27](=[O:29])[CH3:28])[O:22][C:21]3=[O:30])=[CH:16][C:15]=2[F:31])[CH2:12][CH2:13]1)([O-:5])=[O:4]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 24758Sodium hydrideHCID 54375226N-[(5S)-3-[3-fluoro-4-(4-oxopiperidinyl)phenyl]-2-oxo-5-oxazolidinyl]methylacetamide

Product 1

HCID 11418409(S)-N-{3-[4-(4-Nitromethyl-4-hydroxypiperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamideYield 17%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of sodium hydride (0.72 g, 17.0 mmol) in dry tetrahydrofuran (40 ml) was added nitromethane (12.4 mmol) at 0° C. temperature. It was further stirred for 30 minutes and then (S)—N-{3-[4-(4-oxo-piperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (7.2 mmol) was added. The reaction mixture was stirred at 65° C. for 24 hours. The reaction mixture was poured on to crushed ice. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (2×20 ml). The removal of solvent afforded a crude compound, which was purified by column chromatography over silica gel to afford title compound in 17% yield. M.P. 186-187° C. and MS (M+1)=384 (MH+, 100%) M.F.=C18H23FN4O6.

Workup

  1. stirringThe reaction mixture was stirred at 65° C. for 24 hours
  2. additionThe reaction mixture was poured on
  3. customto crushed ice
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate (2×20 ml)
  6. customThe removal of solvent
  7. customafforded a crude compound, which
  8. customwas purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-f9c2d497c2df496b9b837b748557dc2c
Source dataset
uspto-grants-2014_05
Patent number
US08729269B2

Reaction notes

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