2-Aminopropanol → Rac-4-methyl-2-[2-(5-methyl-3-phenyl-isoxazol-4-yl)-ethyl]-thiazole-5-carboxylic acid (2-hydroxy-1-methyl-ethyl)-amide

HRID 1923491ノート

反応式

HRID 1923491 の反応式
[CH3:1][C:2]1[N:3]=[C:4]([CH2:10][CH2:11][C:12]2[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:14][O:15][C:16]=2[CH3:17])[S:5][C:6]=1[C:7](O)=[O:8].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[NH2:55][CH:56]([CH3:59])[CH2:57][OH:58]>CN(C=O)C>[OH:58][CH2:57][CH:56]([NH:55][C:7]([C:6]1[S:5][C:4]([CH2:10][CH2:11][C:12]2[C:13]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[N:14][O:15][C:16]=2[CH3:17])=[N:3][C:2]=1[CH3:1])=[O:8])[CH3:59]

参加物

6

反応物 4

HCID 51262-AminopropanolHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66643564HCID 66643564、化合物

生成物 1

HCID 59568489Rac-4-methyl-2-[2-(5-methyl-3-phenyl-isoxazol-4-yl)-ethyl]-thiazole-5-carboxylic acid (2-hydroxy-1-methyl-ethyl)-amide収率 50%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4-methyl-2-[2-(5-methyl-3-phenyl-isoxazol-4-yl)-ethyl]-thiazole-5-carboxylic acid (100 mg, 0.31 mmol) in DMF (3 mL) were added 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (108 mg, 0.33 mmol), N,N-diisopropyl ethyl amine (197 μL, 1.67 mmol) and rac-2-amino-1-propanol (30 mg, 0.40 mmol). The resulting reaction mixture was stirred for 2 h. The reaction mixture was extracted with ethyl acetate. The combined organic layers were then dried over sodium sulfate, filtered and evaporated. Concentration and purification by chromatography (silica, 0 to 2.5% methanol in dichlormethane) afforded the title compound (59 mg, 50%) as a colourless oil. MS: m/e=386.2 [M+H]+.

後処理

  1. customThe resulting reaction mixture
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. dry with materialThe combined organic layers were then dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. concentrationConcentration and purification by chromatography (silica, 0 to 2.5% methanol in dichlormethane)

出典と根拠

ORDレコード
ord-844d4cab345646e483cb02d32ce93d81
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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