2,4,6-Tri-t-butyl-1-bromobenzene → Racemic 3-{4-[1-(2,4,6-tri-t-butyl-phenoxy)-5,5,5-trifluoro-pentyl]-benzoylamino}-propionic acid methyl ester

HRID 1160937ノート

反応式

HRID 1160937 の反応式
[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][NH:6][C:7](=[O:38])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([O:22]C2C=CC(B3OC(C)(C)C(C)(C)O3)=CC=2)[CH2:15][CH2:16][CH2:17][C:18]([F:21])([F:20])[F:19])=[CH:10][CH:9]=1.Br[C:41]1[C:46]([C:47]([CH3:50])([CH3:49])[CH3:48])=[CH:45][C:44]([C:51]([CH3:54])([CH3:53])[CH3:52])=[CH:43][C:42]=1[C:55]([CH3:58])([CH3:57])[CH3:56].[F-].[K+]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][NH:6][C:7](=[O:38])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([O:22][C:41]2[C:46]([C:47]([CH3:50])([CH3:49])[CH3:48])=[CH:45][C:44]([C:51]([CH3:54])([CH3:53])[CH3:52])=[CH:43][C:42]=2[C:55]([CH3:58])([CH3:57])[CH3:56])[CH2:15][CH2:16][CH2:17][C:18]([F:20])([F:21])[F:19])=[CH:10][CH:9]=1

参加物

5

反応物 3

HCID 1380892,4,6-Tri-t-butyl-1-bromobenzeneHCID 522689Potassium FluorideHCID 671534183-(4-{5,5,5-Trifluoro-1-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-phenoxy]-pentyl}-benzoylamino)-propionic acid methyl ester

生成物 1

HCID 67153635Racemic 3-{4-[1-(2,4,6-tri-t-butyl-phenoxy)-5,5,5-trifluoro-pentyl]-benzoylamino}-propionic acid methyl ester

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of racemic 3-(4-{5,5,5-Trifluoro-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]-pentyl}-benzoylamino)-propionic acid methyl ester (0.300 g, 0.550 mmol) in toluene (3.0 mL) is added palladium tetrakis triphenylphosphine (0.0316 g, 0.030 mmol), 2-bromo-1,3,5-tri-tert-butyl-benzene (0.353 g, 1.09 mmol), and potassium fluoride (0.063 g, 1.09 mmol). The reaction is purged with nitrogen three times and heated to reflux under nitrogen. At reflux, water (1.0 mL) is added to the reaction and the reaction is allowed to reflux under nitrogen. The reaction is monitored by HPLC, and upon completion, allowed to cool to room temperature. The reaction is diluted with ethyl acetate and celite is added, followed by water. This mixture is then filtered through a pad of celite. The solution is poured into a separatory funnel and the organic layer is washed with water and brine. The organic layer is dried over anhydrous sodium sulfate and concentrated. The product is purified by flash column chromatography (0.333 g, 0.500 mmol).

後処理

  1. customThe reaction is purged with nitrogen three times
  2. temperatureheated
  3. temperatureto reflux under nitrogen
  4. temperatureAt reflux
  5. additionwater (1.0 mL) is added to the reaction
  6. temperatureto reflux under nitrogen
  7. additionThe reaction is diluted with ethyl acetate and celite
  8. additionis added
  9. filtrationThis mixture is then filtered through a pad of celite
  10. additionThe solution is poured into a separatory funnel
  11. washthe organic layer is washed with water and brine
  12. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  13. concentrationconcentrated
  14. customThe product is purified by flash column chromatography (0.333 g, 0.500 mmol)

出典と根拠

ORDレコード
ord-486993fed9cd4e4e98618cc9ccb2d922
出典データセット
uspto-grants-2010_10
特許番号
US07816557B2

反応ノート

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