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

HRID 220057Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 220057
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:9]=[C:8]([CH:10]2[CH2:15][CH:14]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=3)[CH2:13][N:12]([C:27]([N:29]3[CH2:34][CH2:33][S:32][CH2:31][CH2:30]3)=[O:28])[CH2:11]2)[O:7][N:6]=1.ClC1C=CC=C(C(OO)=[O:43])C=1>>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:9]=[C:8]([CH:10]2[CH2:15][CH:14]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23]([F:25])([F:24])[F:26])=[CH:18][CH:17]=3)[CH2:13][N:12]([C:27]([N:29]3[CH2:34][CH2:33][S:32](=[O:43])[CH2:31][CH2:30]3)=[O:28])[CH2:11]2)[O:7][N:6]=1

Komponenten

3

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 59606583{3-[3-(2-Methoxyethyl)-1,2,4-oxadiazol-5-yl]-5-[4-(2,2,2-trifluoroethyl)phenyl]piperidin-1-yl}-(thiomorpholin-4-yl)methanone

Produkt 1

HCID 59606567{3-[3-(2-Methoxyethyl)-1,2,4-oxadiazol-5-yl]-5-[4-(2,2,2-trifluoroethyl)phenyl]piperidin-1-yl}(1-oxidothiomorpholin-4-yl)methanoneAusbeute 39,8 %

Versuchsvorschrift

113 mg (0.227 mmol) of the compound from Example 47A were reacted according to General Method 1 with 70.4 mg (0.204 mmol) of meta-chloroperbenzoic acid. Enantiomer separation of 108 mg of the racemate according to Method 9D gave 37.1 mg of the title compound from Example 46 (Enantiomer 1) and 41.8 mg of the title compound from Example 47 (Enantiomer 2).

Aufarbeitung

  1. customEnantiomer separation of 108 mg of the racemate

Quellen und Nachweise

ORD-Eintrag
ord-8affb1c7b3b34b0e9c4f073868d62513
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202862B2

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