(5R)-3-[3-fluoro-4-(3-hydroxyazetidin-1-yl)phenyl]-5-(isoxazol-3-yloxymethyl)oxazolidin-2-one → 3-(3-Fluoro-4-(2-methyl-imidazol-1-yl)phenyl)-5(r)-(isoxazol-3-yloxymethyl)oxazolidin-2-one

HRID 1167468Notes

Reaction equation

HRID 1167468 reaction equation
O[CH:2]1[CH2:5][N:4]([C:6]2[CH:11]=[CH:10][C:9]([N:12]3[CH2:16][C@H:15]([CH2:17][O:18][C:19]4[CH:23]=[CH:22][O:21][N:20]=4)[O:14][C:13]3=[O:24])=[CH:8][C:7]=2[F:25])[CH2:3]1.FC1C=C(N2C[C@H](CO)OC2=O)C=C[C:32]=1[N:33]1C=CN=C1C>>[F:25][C:7]1[CH:8]=[C:9]([N:12]2[CH2:16][C@H:15]([CH2:17][O:18][C:19]3[CH:23]=[CH:22][O:21][N:20]=3)[O:14][C:13]2=[O:24])[CH:10]=[CH:11][C:6]=1[N:4]1[CH:3]=[CH:32][N:33]=[C:5]1[CH3:2]

Participants

3

Reactant 2

HCID 497421(5R)-3-[3-fluoro-4-(3-hydroxyazetidin-1-yl)phenyl]-5-(isoxazol-3-yloxymethyl)oxazolidin-2-oneHCID 21356557(5R)-3-(3-Fluoro-4-(2-methylimidazol-1-yl)phenyl)-5-hydroxymethyloxazolidin-2-one

Product 1

HCID 699831893-(3-Fluoro-4-(2-methyl-imidazol-1-yl)phenyl)-5(r)-(isoxazol-3-yloxymethyl)oxazolidin-2-one

Procedure

Using essentially the same procedure as for the intermediate of Example 65, but starting with 3-(3-fluoro-4-(2-methyl-imidazol-1-yl)phenyl)-5(R)-hydroxymethyloxazolidin-2-one (202 mg, 0.69 mmol), and purifying by chromatography on a 10 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 0 to 2.5% MeOH in dichloromethane, the title compound was prepared (137 mg).

Workup

  1. custompurifying by chromatography on a 10 g silica Mega Bond Elut® column
  2. washeluting with a gradient
  3. temperatureincreasing in polarity from 0 to 2.5% MeOH in dichloromethane

Sources & evidence

ORD record
ord-ad97199a624f4a19942add03c6b27245
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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