Methanol → 3-{4-[4-(3-hydroxy-propyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-methoxy-phenyl}-4H-[1,2,4]oxadiazol-5-one

HRID 2263404노트

반응식

HRID 2263404 반응식
C([O:8][CH2:9][CH2:10][CH2:11][C:12]1[N:13]=[C:14]([C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=2)[S:15][C:16]=1[CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[NH:29][C:28](=[O:30])[O:27][N:26]=2)=[C:21]([O:31][CH3:32])[CH:20]=1)C1C=CC=CC=1.I[Si](C)(C)C.CO.C(=O)(O)[O-].[Na+]>ClCCl>[OH:8][CH2:9][CH2:10][CH2:11][C:12]1[N:13]=[C:14]([C:33]2[CH:34]=[CH:35][C:36]([C:39]([F:40])([F:41])[F:42])=[CH:37][CH:38]=2)[S:15][C:16]=1[CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[NH:29][C:28](=[O:30])[O:27][N:26]=2)=[C:21]([O:31][CH3:32])[CH:20]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 85247Trimethylsilyl iodideHCID 516892Sodium BicarbonateHCID 1361499763-{4-[4-(3-benzyloxy-propyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-methoxy-phenyl}-4H-[1,2,4]oxadiazol-5-one

생성물 1

HCID 1361499373-{4-[4-(3-hydroxy-propyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-methoxy-phenyl}-4H-[1,2,4]oxadiazol-5-one수율 39.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

118 mg of 3-{4-[4-(3-benzyloxy-propyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-methoxy-phenyl}-4H-[1,2,4]oxadiazol-5-one were dissolved in 14 mL of dichloromethane by heating and allowing to cool down to room temperature. To the resulting solution was added 144 μL of iodotrimethylsilane. The resulting mixture was stirred at room temperature for 6.5 h and 6 mL of methanol were added followed by a saturated aqueous solution of sodium bicarbonate. The mixture was stirred for 1 h, filtered and concentrated under reduced pressure. Dichloromethane/water were added to the residue. The organic layer was separated and the aqueous layer extracted three times with dichloromethane. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (dichloromethane 90/methanol 10) to give 40 mg of 3-{4-[4-(3-hydroxy-propyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-methoxy-phenyl}-4H-[1,2,4]oxadiazol-5-one.

후처리

  1. temperatureby heating
  2. stirringThe mixture was stirred for 1 h
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. additionDichloromethane/water were added to the residue
  6. customThe organic layer was separated
  7. extractionthe aqueous layer extracted three times with dichloromethane
  8. dry with materialThe combined organic extracts were dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe crude product was purified by column chromatography on silica gel (dichloromethane 90/methanol 10)

출처 및 근거

ORD 기록
ord-d40ad7228eb9404d90faf498380a4789
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07851493B2

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