Potassium Hydroxide → HCID 178463324, compound
Reaction equation
[F:1][C:2]([F:50])([F:49])[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[N:31]([CH2:46][CH3:47])[C:32]([C@H:34]3[CH2:39][CH2:38][C@H:37]([CH2:40][C:41]([O:43]CC)=[O:42])[CH2:36][CH2:35]3)=[O:33])[C@H:14]2[CH3:48])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[OH-].[K+]>>[F:12][C:9]([F:10])([F:11])[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]([CH2:46][CH3:47])[C:32]([C@H:34]3[CH2:39][CH2:38][C@H:37]([CH2:40][C:41]([OH:43])=[O:42])[CH2:36][CH2:35]3)=[O:33])[C@H:14]2[CH3:48])[CH:4]=[C:3]([C:2]([F:1])([F:50])[F:49])[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](ethyl)amino]carbonyl}cyclohexyl)acetate (100 mg; 0.138 mmol) was treated with 4 M KOH (1 mL) as in EXAMPLE 87 to afford (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)acetic acid as a white solid. LCMS=699.0 (M+1)+. 1H NMR (CDCl3, 500 MHz, mixture of atropisomers): δ 7.92 (s, 1 H), 7.80 (s, 1 H), 7.75 (s, 1H), 7.29-7.22 (m, 1 H), 7.19-7.17 (m, 1 H), 7.15-7.11 (m, 1 H), 5.67 (d, J=8.3 Hz, 1 H), 4.93 (d, J=14.9 Hz, 1 H), 4.25-4.10 (m, 2 H), 3.91 (d, J=14.9 Hz, 1 H), 3.54-3.46 (m, 1 H), 3.09-3.01 (m, 1 H), 2.68-2.61 (m, 1 H), 2.27-2.24 (m, 1 H), 2.15-2.11 (m, 1 H), 1.96-1.51 (m, 6 H), 1.26-1.21 (m, 1 H), 1.17-1.12 (m, 3 H), 0.83-0.67 (m, 4 H).
Sources & evidence
- ORD record
- ord-57a34f336c7d4f0eab6745535ff5e6c0
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07781426B2
Reaction notes
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