1,1'-(Azodicarbonyl)dipiperidine → 5-(4-(5-Cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-ylmethoxy)-2-methyl-phenyl)-thiophene-2-carboxylic acid methyl ester

HRID 250284ノート

反応式

HRID 250284 の反応式
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=3[Cl:16])[C:5]=2[CH2:17][OH:18])[CH2:3][CH2:2]1.[CH3:19][O:20][C:21]([C:23]1[S:24][C:25]([C:28]2[CH:33]=[CH:32][C:31](O)=[CH:30][C:29]=2[CH3:35])=[CH:26][CH:27]=1)=[O:22].C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1(C)C=CC=CC=1>[CH3:19][O:20][C:21]([C:23]1[S:24][C:25]([C:28]2[CH:33]=[CH:32][C:31]([O:18][CH2:17][C:5]3[C:6]([C:9]4[C:10]([Cl:16])=[CH:11][CH:12]=[CH:13][C:14]=4[Cl:15])=[N:7][O:8][C:4]=3[CH:1]3[CH2:3][CH2:2]3)=[CH:30][C:29]=2[CH3:35])=[CH:26][CH:27]=1)=[O:22]

参加物

5

反応物 3

HCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 45790382(5-Cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-yl)methanolHCID 574432865-(4-Hydroxy-2-methyl-phenyl)-thiophene-2-carboxylic acid methyl ester

生成物 1

HCID 580883565-(4-(5-Cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-ylmethoxy)-2-methyl-phenyl)-thiophene-2-carboxylic acid methyl ester収率 45.4%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

To a solution of (5-cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-yl)-methanol (0.188 g, 0.66 mmol), 5-(4-hydroxy-2-methyl-phenyl)-thiophene-2-carboxylic acid methyl ester (0.15 g, 0.60 mmol), and tri-N-butyl-phosphine (0.16 g, 0.79 mmol) in toluene (2 mL) is added a solution of ADDP (0.2 g, 0.79 mmol) in 1 mL of toluene. The reaction is stirred overnight. The reaction mixture is partitioned between ethyl acetate and water and the layers are separated. The organic layer is washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield a crude oil. The oil is chromatographed using a gradient of 10% ethyl acetate in hexanes to 40% ethyl acetate in hexanes to yield the title compound (0.14 g, 41%). ES/MS m/e 514.0 (M+1).

後処理

  1. customThe reaction mixture is partitioned between ethyl acetate and water
  2. customthe layers are separated
  3. washThe organic layer is washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto yield a crude oil
  8. customThe oil is chromatographed

出典と根拠

ORDレコード
ord-11ec63371a9043fba1638f1c68e218c1
出典データセット
uspto-grants-2011_01
特許番号
US07863302B2

反応ノート

読み込み中…