N-[3-(3-fluoro-4-hydroxy-phenyl)-2-oxo-oxazolidin-5(S)-ylmethyl]-acetamide → N-{3-[3-Fluoro-4-(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-ylmethoxy)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide

HRID 1446072Notes

Reaction equation

HRID 1446072 reaction equation
BrC1C=CC(O[CH2:7][C:8]2([CH3:19])[O:12][C:11]3=[N:13][C:14]([N+:16]([O-:18])=[O:17])=[CH:15][N:10]3[CH2:9]2)=CC=1.[F:22][C:23]1[CH:24]=[C:25]([N:30]2[CH2:34][C@H:33]([CH2:35][NH:36][C:37](=[O:39])[CH3:38])[O:32][C:31]2=[O:40])[CH:26]=[CH:27][C:28]=1[OH:29]>>[F:22][C:23]1[CH:24]=[C:25]([N:30]2[CH2:34][CH:33]([CH2:35][NH:36][C:37](=[O:39])[CH3:38])[O:32][C:31]2=[O:40])[CH:26]=[CH:27][C:28]=1[O:29][CH2:7][C:8]1([CH3:19])[O:12][C:11]2=[N:13][C:14]([N+:16]([O-:18])=[O:17])=[CH:15][N:10]2[CH2:9]1

Participants

3

Reactant 2

HCID 57754832N-[3-(3-fluoro-4-hydroxy-phenyl)-2-oxo-oxazolidin-5(S)-ylmethyl]-acetamideHCID 685456062-(4-Bromo-phenoxymethyl)-2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazole

Product 1

HCID 68546314N-{3-[3-Fluoro-4-(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-ylmethoxy)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide

Procedure

The title compound was prepared by following the same procedure as described in the preparation of Example 36, 2-(4-Bromo-phenoxymethyl)-2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazole (prepared similarly as described by Sasaki, H. et al: Journal of Medicinal Chemistry (2006), 49(26), 7854-7860), except N-[3-(3-fluoro-4-hydroxy-phenyl)-2-oxo-oxazolidin-5(S)-ylmethyl]-acetamide was used in the place of 4-bromophenol. The product isolated as a solid. ESI MS m/z 450 (M+H+).

Workup

  1. customprepared similarly
  2. customThe product isolated as a solid

Sources & evidence

ORD record
ord-0e45da3f467b4f62b4610fe1138329a1
Source dataset
uspto-grants-2010_02
Patent number
US07666864B2

Reaction notes

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