m-Chloroperbenzoic acid → {3-[3-(2-Methoxyethoxy)-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethoxy)phenyl]piperidin-1-yl}-(1-oxidothiomorpholin-4-yl)methanone

HRID 661292Notes

Reaction equation

HRID 661292 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[N:10]=[C:9]([CH:11]2[CH2:16][CH:15]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[CH2:14][N:13]([C:28]([N:30]3[CH2:35][CH2:34][S:33][CH2:32][CH2:31]3)=[O:29])[CH2:12]2)[O:8][N:7]=1.ClC1C=CC=C(C(OO)=[O:44])C=1>>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[N:10]=[C:9]([CH:11]2[CH2:16][CH:15]([C:17]3[CH:18]=[CH:19][C:20]([O:23][C:24]([F:26])([F:27])[F:25])=[CH:21][CH:22]=3)[CH2:14][N:13]([C:28]([N:30]3[CH2:35][CH2:34][S:33](=[O:44])[CH2:32][CH2:31]3)=[O:29])[CH2:12]2)[O:8][N:7]=1

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 58116577{3-[3-(2-Methoxyethoxy)-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethoxy)phenyl]piperidin-1-yl}-(thiomorpholin-4-yl)methanone

Product 1

HCID 58116572{3-[3-(2-Methoxyethoxy)-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethoxy)phenyl]piperidin-1-yl}-(1-oxidothiomorpholin-4-yl)methanoneYield 17.9%

Procedure

60.0 mg (0.116 mmol) of the compound from Example 42 were reacted according to General Method 2 with 36.1 mg (0.105 mmol) of meta-chloroperbenzoic acid. Enantiomer separation of the racemate according to Method 2D gave 10.0 mg of the title compound of Example 43 (enantiomer 1).

Workup

  1. customEnantiomer separation of the racemate

Sources & evidence

ORD record
ord-896cb7ffbed64aaf9dd47710b6721291
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

Loading…