(S)-N-[3-(3-Fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide → N-({(5S)-2-oxo-3-[4-(2-oxopiperidin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)acetamide

HRID 10830Notes

Reaction equation

HRID 10830 reaction equation
I[C:2]1C=C[C:5]([N:8]2C[C@H](CNC(=O)OC(C)(C)C)O[C:9]2=[O:22])=[CH:4][CH:3]=1.F[C:24]1[CH:25]=[C:26]([N:31]2[CH2:35][C@H:34]([CH2:36][NH:37][C:38](=[O:40])[CH3:39])[O:33][C:32]2=[O:41])[CH:27]=[CH:28][C:29]=1I>>[O:41]=[C:32]1[N:31]([C:26]2[CH:27]=[CH:28][C:29]([CH:3]3[CH2:4][CH2:5][NH:8][C:9](=[O:22])[CH2:2]3)=[CH:24][CH:25]=2)[CH2:35][C@H:34]([CH2:36][NH:37][C:38](=[O:40])[CH3:39])[O:33]1

Participants

3

Reactant 2

HCID 11222662(S)-N-[3-(3-Fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamideHCID 86591790tert-butyl [(5S)-3-(4-iodophenyl)-2-oxo-1,3-oxazolidin-5-yl]methylcarbamate

Product 1

HCID 10019593N-({(5S)-2-oxo-3-[4-(2-oxopiperidin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)acetamide

Procedure

N-({(5S)-2-oxo-3-[4-(2-oxopiperidin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)acetamide is prepared as described in the route described in Example 16 substituting tert-butyl [(5S)-3-(4-iodophenyl)-2-oxo-1,3-oxazolidin-5-yl]methylcarbamate for N-{[(5S)-3-(3-fluoro-4-iodophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide. 1H-NMR (DMSO) δ: 8.25, 7.55, 7.47, 7.30, 4.70, 4.10, 3.73, 3.40, 3.17, 3.02, 2.31, 1.87, 1.83

Sources & evidence

ORD record
ord-603ab36590b94febb01366d65d2beff1
Source dataset
uspto-grants-2006_08
Patent number
US07094900B2

Reaction notes

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