Sodium hydride → (4S)-3-{[4'-fluoro-5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4-(4-methylbenzyl)-1,3-oxazolidin-2-one
Reaction equation
[CH3:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][C@H:7]2[CH2:11][O:10][C:9](=[O:12])[NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:18][C:19]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:20]=1[C:29]1[CH:34]=[C:33]([CH:35]([CH3:37])[CH3:36])[C:32]([F:38])=[CH:31][C:30]=1[O:39][CH3:40]>>[F:38][C:32]1[C:33]([CH:35]([CH3:37])[CH3:36])=[CH:34][C:29]([C:20]2[CH:21]=[CH:22][C:23]([C:25]([F:27])([F:28])[F:26])=[CH:24][C:19]=2[CH2:18][N:8]2[C@@H:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:14][CH:13]=3)[CH2:11][O:10][C:9]2=[O:12])=[C:30]([O:39][CH3:40])[CH:31]=1Participants
Reactant 3
Product 1
Procedure
(4S)-4-(4-methylbenzyl)-1,3-oxazolidin-2-one (Step B, 14 mg, 0.074 mmol) was treated with sodium hydride (60% in oil, 6.2 mg, 0.154 mmol) and 2′-(bromomethyl)-4-fluoro-5-isopropyl-2-methoxy-4′-(trifluoromethyl)biphenyl (Intermediate 10, 25 mg, 0.062 mmol) as described in Example 305 to afford (4S)-3-{[4′-fluoro-5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4-(4-methylbenzyl)-1,3-oxazolidin-2-one as clear gum. LCMS=516.4 (M+1)+. 1H NMR (CDCl3, 500 MHz, mixture of atropisomers) δ 7.65-7.60 (m, 1H), 7.53 (s, 1H), 7.35-7.32 (m, 1H), 7.06-7.20 (m, 2H), 6.82-6.75 (m, 2H), 6.69 (d, J=11.7 Hz, 1H), 4.67 (d, J=15.8 Hz, 1H), 4.06 (d, J=15.8 Hz, 1H), 4.04-4.00 (m, 1H), 3.96-3.93 (m, 1H), 3.73 (s, 3H), 3.55-3.48 (m, 1H), 3.23-3.15 (m, 1H), 2.63 (dd, J=13.5, 3.6 Hz, 1H), 2.35 (d, J=13.5 Hz, 1H), 2.29 (s, 3H), 1.25-1.13 (m, 6H).
Sources & evidence
- ORD record
- ord-7630adb7707a41f9a6594a7bc35e6588
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07652049B2
Reaction notes
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