(S)-N-[3-(3-Fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide → HCID 59749512, compound

HRID 747231Notes

Reaction equation

HRID 747231 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][NH:15][C:16](=[O:18])[CH3:17])[O:11][C:10]2=[O:19])[CH:5]=[CH:6][C:7]=1I.[Si:20]([O:27][CH2:28][C@@H:29]1[O:33][C:32](=[O:34])[N:31]([C:35]2[CH:40]=[CH:39][C:38]([Sn](C)(C)C)=[C:37]([F:45])[CH:36]=2)[CH2:30]1)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>>[Si:20]([O:27][CH2:28][C@@H:29]1[O:33][C:32](=[O:34])[N:31]([C:35]2[CH:40]=[CH:39][C:38]([C:7]3[CH:6]=[CH:5][C:4]([N:9]4[CH2:13][C@H:12]([CH2:14][NH:15][C:16](=[O:18])[CH3:17])[O:11][C:10]4=[O:19])=[CH:3][C:2]=3[F:1])=[C:37]([F:45])[CH:36]=2)[CH2:30]1)([C:23]([CH3:26])([CH3:24])[CH3:25])([CH3:22])[CH3:21]

Participants

3

Reactant 2

HCID 11222662(S)-N-[3-(3-Fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamideHCID 59749469HCID 59749469, compound

Product 1

HCID 59749512HCID 59749512, compoundYield 57.7%

Procedure

Using essentially the same procedure as Example 28, but starting from N-{[(5S)-3-(3-fluoro-4-iodophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide (0.38 g, 1.00 mM) and adding (5R)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-3-[3-fluoro-4-(trimethylstannyl)phenyl]-1,3-oxazolidin-2-one (0.73 g, 1.50 mM) gave the title compound as a light yellow solid (0.334 g).

Sources & evidence

ORD record
ord-813fa6faeba145d4ada2d2d24f142285
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

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