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

HRID 1923490ノート

反応式

HRID 1923490 の反応式
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

参加物

5

反応物 3

HCID 16682925TrimethylaluminumHCID 18664284(3S)-oxolan-3-amine hydrochlorideHCID 66643564HCID 66643564、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒3 回

反応条件

温度
90 °C

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-0b0ecb4c038149969980bd3d723f020d
出典データセット
uspto-grants-2012_05
特許番号
US08178522B2

反応ノート

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