N-({(5S)-2-Oxo-3-[4-(trimethylstannyl)phenyl]-1,3-oxazolidin-5-yl}methyl)acetamide → N-[((5S)-3-{4'-[(5R)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4,5-dihydroisoxazol-3-yl]-1,1'-biphenyl-4-yl}-2-oxo-1,3-oxazolidin-5-yl)methyl]acetamide
Reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([Sn](C)(C)C)=[CH:9][CH:8]=2)[CH2:5][C@H:4]([CH2:17][NH:18][C:19](=[O:21])[CH3:20])[O:3]1.Br[C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH2:33][C@H:32]([CH2:34][O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])[O:31][N:30]=2)=[CH:25][CH:24]=1>>[Si:36]([O:35][CH2:34][C@@H:32]1[O:31][N:30]=[C:29]([C:26]2[CH:25]=[CH:24][C:23]([C:10]3[CH:11]=[CH:12][C:7]([N:6]4[CH2:5][C@H:4]([CH2:17][NH:18][C:19](=[O:21])[CH3:20])[O:3][C:2]4=[O:1])=[CH:8][CH:9]=3)=[CH:28][CH:27]=2)[CH2:33]1)([C:39]([CH3:42])([CH3:40])[CH3:41])([CH3:38])[CH3:37]Participants
3
Reactant 2
Product 1
Procedure
The procedure of Example 41, but starting from N-({(5S)-2-oxo-3-[4-(trimethylstannyl)phenyl]-1,3-oxazolidin-5-yl}methyl)acetamide (476 mg, 1.20 mM) and (5R)-3-(4-bromophenyl)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4,5-dihydroisoxazole (370 mg. 1.00 mM) was used to give the desired product after 7 hours at 90° C. Purification by chromatography on silica gel using 90% ethyl acetate/hexanes gave 398 mg of the title product.
Sources & evidence
- ORD record
- ord-740cf08a78ca4e00913f48aea44b02b4
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07396847B2
Reaction notes
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