Trimethylaluminum → (s)-4-Methyl-2-[2-(5-methyl-3-phenyl-isoxazol-4-yl)-ethyl]-thiazole-5-carboxylic acid (tetrahydro-furan-3-yl)-amide

HRID 1923490노트

반응식

HRID 1923490 반응식
Cl.[O:2]1[CH2:6][CH2:5][C@H:4]([NH2:7])[CH2:3]1.C[Al](C)C.[CH3:12][C:13]1[N:14]=[C:15]([CH2:21][CH2:22][C:23]2[C:24]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[N:25][O:26][C:27]=2[CH3:28])[S:16][C:17]=1[C:18](O)=[O:19]>C1(C)C=CC=CC=1>[O:2]1[CH2:6][CH2:5][C@H:4]([NH:7][C:18]([C:17]2[S:16][C:15]([CH2:21][CH2:22][C:23]3[C:24]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[N:25][O:26][C:27]=3[CH3:28])=[N:14][C:13]=2[CH3:12])=[O:19])[CH2:3]1

참가 물질

5

반응물 3

HCID 16682925TrimethylaluminumHCID 18664284(3S)-oxolan-3-amine hydrochlorideHCID 66643564HCID 66643564, 화합물

생성물 1

HCID 49782926(s)-4-Methyl-2-[2-(5-methyl-3-phenyl-isoxazol-4-yl)-ethyl]-thiazole-5-carboxylic acid (tetrahydro-furan-3-yl)-amide수율 45.8%

시약·촉매·용매 1

HCID 1140Toluene용매3회

반응 조건

온도
90 °C

실험 절차

To a stirred suspension of (S)-tetrahydrofuran-3-amine HCl (127 mg, 1.0 mmol) in toluene (2 mL) under argon at room temperature was added trimethylaluminium (1 mL of a 2M solution in toluene, 2.0 mmol). After 2 h, a solution of 4-methyl-2-[2-(5-methyl-3-phenyl-isoxazol-4-yl)-ethyl]-thiazole-5-carboxylic acid (130 mg, 0.39 mmol) in toluene (4 mL) was added and the reaction mixture warmed to 90° C. After 2 h, the reaction mixture was cooled, quenched with ice water and extracted with dichloromethane. The combined extracts were washed with Seignette's salt solution then dried, filtered, and concentrated. Purification by chromatography (silica, 0 to 10% methanol in dichloromethane) gave the title compound (71 mg, 45%) as a colourless oil. MS: m/e=398.1 [M+H]+.

후처리

  1. waitAfter 2 h
  2. temperaturethe reaction mixture was cooled
  3. customquenched with ice water
  4. extractionextracted with dichloromethane
  5. washThe combined extracts were washed with Seignette's salt solution
  6. customthen dried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by chromatography (silica, 0 to 10% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-0b0ecb4c038149969980bd3d723f020d
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178522B2

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