Water → 3-{4-[4-Methanesulfinylmethyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-methoxy-phenyl}-4h-1,2,4-oxadiazol-5-one

HRID 2263427ノート

反応式

HRID 2263427 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][C:11]2[S:15][C:14]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)=[N:13][C:12]=2[CH2:26][S:27][CH3:28])[CH:6]=[CH:5][C:4]=1[C:29]1[NH:33][C:32](=[O:34])[O:31][N:30]=1.ClC1C=CC=C(C(OO)=[O:43])C=1.O>CN(C)C=O>[CH3:28][S:27]([CH2:26][C:12]1[N:13]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:23])([F:24])[F:25])=[CH:18][CH:17]=2)[S:15][C:11]=1[CH2:10][O:9][C:7]1[CH:6]=[CH:5][C:4]([C:29]2[NH:33][C:32](=[O:34])[O:31][N:30]=2)=[C:3]([O:2][CH3:1])[CH:8]=1)=[O:43]

参加物

5

反応物 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 1354464043-{2-Methoxy-4-[4-methylsulfanylmethyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-4h-1,2,4-oxadiazol-5-one

生成物 1

HCID 1361499433-{4-[4-Methanesulfinylmethyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-methoxy-phenyl}-4h-1,2,4-oxadiazol-5-one収率 75.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 32 mg of 3-{2-methoxy-4-[4-methylsulfanylmethyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-4H-1,2,4-oxadiazol-5-one in 4 mL of dimethylformamide was added 15 mg of metachloroperbenzoic acid. The resulting mixture was stirred for 45 min at room temperature, then poured into water and extracted with dichloromethane. The organic extracts were washed with a saturated aqueous solution if sodium bicarbonate and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (gradient of methanol in dichloromethane) to give 25 mg of 3-{4-[4-methanesulfinylmethyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-methoxy-phenyl}-4H-1,2,4-oxadiazol-5-one as a white solid which was further purified by trituration with diisopropyl ether.

後処理

  1. extractionextracted with dichloromethane
  2. washThe organic extracts were washed with a saturated aqueous solution if sodium bicarbonate
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by column chromatography on silica gel (gradient of methanol in dichloromethane)

出典と根拠

ORDレコード
ord-9c8d20054c6343e58f9a38526a69f73e
出典データセット
uspto-grants-2010_12
特許番号
US07851493B2

反応ノート

読み込み中…