Iodoethane → HCID 178471799, compound
Reaction equation
[F:1][C:2]([F:48])([F:47])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([O:26][C:27]([F:30])([F:29])[F:28])[CH:23]=[CH:22][C:21]=3[NH:31][C:32]([C@H:34]3[CH2:39][CH2:38][C@H:37]([CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:36][CH2:35]3)=[O:33])[C@H:14]2[CH3:46])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[H-].[Na+].I[CH2:52][CH3:53]>>[F:12][C:9]([F:11])([F:10])[C:7]1[CH:6]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([O:26][C:27]([F:30])([F:28])[F:29])[CH:23]=[CH:22][C:21]=3[N:31]([CH2:52][CH3:53])[C:32]([C@H:34]3[CH2:39][CH2:38][C@H:37]([CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:36][CH2:35]3)=[O:33])[C@H:14]2[CH3:46])[CH:4]=[C:3]([C:2]([F:1])([F:47])[F:48])[CH:8]=1Participants
Procedure
Ethyl [trans-4-({[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethoxy)phenyl]amino}carbonyl)cyclohexyl]acetate (637 mg; 0-913 mmol) was treated with sodium hydride (60% in oil; 40 mg; 1.0 mmol) and iodoethane (110 mL; 1.37 mmol) as described in EXAMPLE 86 to afford ethyl (trans-4-{[[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethoxy)phenyl](ethyl)amino]carbonyl}cyclohexyl)acetate as a yellow oil. LCMS=727.0 (M+1)+. 1H NMR (CDCl3, 500 MHz, mixture of atropisomers): δ 7.92 (s, 1 H), 7.80 (s, 1 H), 7.74 (s, 1 U), 7.28-7.22 (m, 1 H), 7.19-7.16 (m, 1 H), 7.14-7.11 (m, 1 H), 5.66 (d, J=8.0 Hz, 1 H), 4.92 (d, J=14.9 Hz, 1 H), 4.25 (d, J=16.9 Hz, 1 H), 4.23-4.05 (m, 4 H), 3.54-3.46 (m, 1 H), 3.08-3.00 (m, 1 H), 2.66-2.58 (m, 1 H), 2.22-2.18 (m, 1 H), 2.09-2.06 (m, 1 H), 1.92-1.52 (m, 6 H), 1.26-1.12 (m, 7 H), 0.81-0.66 (m, 4 H).
Sources & evidence
- ORD record
- ord-fa703b1ab07a4d9489ee749d61c77f42
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07781426B2
Reaction notes
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