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

HRID 1026669Notes

Reaction equation

HRID 1026669 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][NH:20][C:21](=[O:23])[CH3:22])[O:16][C:15]3=[O:24])=[CH:10][C:9]=2[F:25])[CH2:4][CH2:3]1.[Br-].O1CCC[CH2:28]1>>[CH3:28][C:2]1([OH:1])[CH2:3][CH2:4][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][NH:20][C:21](=[O:23])[CH3:22])[O:16][C:15]3=[O:24])=[CH:10][C:9]=2[F:25])[CH2:6][CH2:7]1

Participants

4

Reactant 3

HCID 259Bromide ionHCID 8028TetrahydrofuranHCID 54375226N-[(5S)-3-[3-fluoro-4-(4-oxopiperidinyl)phenyl]-2-oxo-5-oxazolidinyl]methylacetamide

Product 1

HCID 11485356(S)-N-{3-[4-(4-methyl-4-hydroxypiperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamideYield 71%

Procedure

The title compound was prepared by reacting (S)—N-{3-[4-(4-oxo-piperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (1.2 mmol) with methylmagnecium bromide (1.32 mmol) in tetrahydrofuran (20 ml) at a temperature 0° C. to 25° C. for twelve hours and by purifying the compound by silica gel column chromatography in 71% yield.

Workup

  1. customat a temperature 0° C. to 25° C.
  2. customfor twelve hours
  3. customby purifying the compound by silica gel column chromatography in 71% yield

Sources & evidence

ORD record
ord-01ccb2de064d41ee893a1b59bab1966d
Source dataset
uspto-grants-2014_05
Patent number
US08729269B2

Reaction notes

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