m-Chloroperbenzoic acid → {3-(3-Ethoxy-1,2,4-oxadiazol-5-yl)-5-[4-(2,2,2-trifluoroethyl)phenyl]piperidin-1-yl}(1-oxidothio-morpholin-4-yl)methanone

HRID 661301Notes

Reaction equation

HRID 661301 reaction equation
[CH2:1]([O:3][C:4]1[N:8]=[C:7]([CH:9]2[CH2:14][CH:13]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=3)[CH2:12][N:11]([C:26]([N:28]3[CH2:33][CH2:32][S:31][CH2:30][CH2:29]3)=[O:27])[CH2:10]2)[O:6][N:5]=1)[CH3:2].ClC1C=CC=C(C(OO)=[O:42])C=1>>[CH2:1]([O:3][C:4]1[N:8]=[C:7]([CH:9]2[CH2:14][CH:13]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=3)[CH2:12][N:11]([C:26]([N:28]3[CH2:29][CH2:30][S:31](=[O:42])[CH2:32][CH2:33]3)=[O:27])[CH2:10]2)[O:6][N:5]=1)[CH3:2]

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 58116557{3-(3-Ethoxy-1,2,4-oxadiazol-5-yl)-5-[4-(2,2,2-trifluoroethyl)phenyl]piperidin-1-yl}-(thiomorpholin-4-yl)methanone

Product 1

HCID 58116532{3-(3-Ethoxy-1,2,4-oxadiazol-5-yl)-5-[4-(2,2,2-trifluoroethyl)phenyl]piperidin-1-yl}(1-oxidothio-morpholin-4-yl)methanoneYield 44.1%

Procedure

129 mg (0.266 mmol) of the compound from Example 64 were reacted according to General Method 2 with 82.7 mg (0.240 mmol) of meta-chloroperbenzoic acid. Enantiomer separation of 132 mg of the racemate according to Method 8D gave 51.0 mg of the title compound from Example 65 (enantiomer 1) and 53.0 mg of the title compound from Example 66 (enantiomer 2).

Workup

  1. customEnantiomer separation of 132 mg of the racemate

Sources & evidence

ORD record
ord-31ad2a4f90264558a8cb24718a487c52
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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