Water → 2-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-thiazole-5-carboxylic acid isopropylamide

HRID 1923646노트

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HRID 1923646 반응식
[H-].[Na+].[CH2:3]([C:7]1[C:11]([CH2:12][OH:13])=[C:10]([CH3:14])[O:9][N:8]=1)[CH2:4][CH2:5][CH3:6].[CH:15]([NH:18][C:19]([C:21]1[S:25][C:24](Cl)=[N:23][CH:22]=1)=[O:20])([CH3:17])[CH3:16].O>C1COCC1>[CH:15]([NH:18][C:19]([C:21]1[S:25][C:24]([O:13][CH2:12][C:11]2[C:7]([CH2:3][CH2:4][CH2:5][CH3:6])=[N:8][O:9][C:10]=2[CH3:14])=[N:23][CH:22]=1)=[O:20])([CH3:17])[CH3:16]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 66599297(3-Butyl-5-methyl-isoxazol-4-yl)-methanolHCID 666437382-Chloro-thiazole-5-carboxylic acid isopropylamide

생성물 1

HCID 666436022-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-thiazole-5-carboxylic acid isopropylamide수율 43%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

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온도
0 °C

실험 절차

To a suspension of NaH (55%, 58 mg, 2.4 mmol) in THF (3 mL) at 0° C., was added a solution of (3-butyl-5-methyl-isoxazol-4-yl)-methanol (169 mg, 1.0 mmol) in THF (3 mL) dropwise. The resulting mixture was stirred for 1 h and then cooled to 0° C. and then a solution of 2-chloro-thiazole-5-carboxylic acid isopropylamide (205 mg, 1.0 mmol) in THF (3 mL) added dropwise and the resulting mixture stirred at room temperature overnight. Water was then added and the resulting mixture extracted with ethyl acetate. The combined organic extracts were dried, filtered and concentrated. Purification by chromatography (silica, 0 to 30% methanol in dichloromethane, then 0 to 60% ethyl acetate in heptane) gave the title compound (145 mg, 43%) as a white solid. MS: m/e=338.4 [M+H]+.

후처리

  1. stirringthe resulting mixture stirred at room temperature overnight
  2. extractionthe resulting mixture extracted with ethyl acetate
  3. customThe combined organic extracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by chromatography (silica, 0 to 30% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-5e80a1d9569f48a19fec74ecd6ad9c30
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178522B2

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