Hydrogen Peroxide → HCID 66672997, compound
Reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[CH:13][C:12]([O:15][CH2:16][CH:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.OO.[F:31][C:32]([F:40])([F:39])C([OH:38])C(F)(F)F>>[F:31][C:32]([F:40])([F:39])[C:23]([OH:25])=[O:24].[CH3:1][S:2]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[CH:13][C:12]([O:15][CH2:16][CH:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)=[O:38]Participants
4
Procedure
The title compound (370 mg, 99%) was prepared as an off-white solid from 1-methylethyl 4-[({6-[4-(methylthio)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarboxylate (prepared as in Example 173, Step 1, 360 mg, 0.9 mmol), 30% H2O2 (aq) (0.612 mL, 5.4 mmol) and 1,1,1,3,3,3-hexafluoro-2-propanol (3 mL) in a manner similar to Example 171, Step 3. 1H NMR (400 MHz, CDCl3): δ 8.50 (d, 1H, J=2.7 Hz), 8.05 (d, 2H, J=8.4 Hz), 7.78-7.71 (m, 3H), 7.45 (dd, 1H, Ja=8.7 Hz, Jb=2.5 Hz), 4.91 (septet, 1H, J=6.2 Hz), 4.21 (bs, 2H), 3.93 (d, 2H, J=6.3 Hz), 2.84-2.72 (m, 5H), 2.09-1.96 (m, 1H), 1.90-1.80 (m, 2H), 1.37-1.20 (m, 8H); LRMS (ESI), m/z 417 (M+H).
Sources & evidence
- ORD record
- ord-f85e547378644d97ab112844ef409598
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08101634B2
Reaction notes
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