Triethylamine → [6-(n-Hexylsulfonoyl)-2-[4-(n-hexylsulfonoyl)phenyl]benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]-phenyl] methanone

HRID 325154

反応式

HRID 325154 の反応式
Cl.O[C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)=[CH:15][CH:14]=3)=[O:12])=[C:9]([C:28]3[CH:33]=[CH:32][C:31](O)=[CH:30][CH:29]=3)[S:8][C:7]=2[CH:35]=1.C(N([CH2:41][CH3:42])CC)C.[CH2:43]([S:49](Cl)(=[O:51])=[O:50])[CH2:44][CH2:45][CH2:46][CH2:47][CH3:48]>CN(C1C=CN=CC=1)C.O1CCCC1>[CH2:43]([S:49]([C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([C:13]3[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)=[CH:17][CH:18]=3)=[O:12])=[C:9]([C:28]3[CH:29]=[CH:30][C:31]([S:49]([CH2:43][CH2:44][CH2:45][CH2:46][CH2:41][CH3:42])(=[O:51])=[O:50])=[CH:32][CH:33]=3)[S:8][C:7]=2[CH:35]=1)(=[O:51])=[O:50])[CH2:44][CH2:45][CH2:46][CH2:47][CH3:48]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 54900Raloxifene HydrochlorideHCID 845041-Hexanesulfonyl chloride

生成物 1

HCID 18357255[6-(n-Hexylsulfonoyl)-2-[4-(n-hexylsulfonoyl)phenyl]benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]-phenyl] methanone

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

In dry tetrahydrofuran (250 ml) 3 g (5.9 mmol) of [6-hydroxy-2-(4-hydroxyphenyl)-benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]-methanone hydrochloride was suspended and 10 mg of DMAP was added. Triethylamine (4 g, 40 mmol) was then added and the reaction mixture was stirred for 20 minutes at room temperature under a nitrogen blanket. n-Hexylsulfonyl chloride (3.6 g, 19.6 mmol) in 25 ml of tetrahydrofuran was slowly added to the reaction mixture. The reaction was allowed to proceed at room temperature and under nitrogen for 3 days. The reaction mixture was evaporated down in vacuo and resuspended in ethyl acetate and washed with water. The organic layer was dried by filtering it through anhydrous sodium sulfate and evaporated to a yellow oil. The oil was dissolved in chloroform and chromatographed (HPLC) on a silica gel column and eluted with a linear gradient starting with chloroform and ending with chloroform-methanol (19:1 v/v). The desired fractions were determined by thin layer chromatography, combined and evaporated down to afford 3.14 g of the title compound as a thick oil.

後処理

  1. waitto proceed at room temperature and under nitrogen for 3 days
  2. customThe reaction mixture was evaporated down in vacuo
  3. washwashed with water
  4. customThe organic layer was dried
  5. filtrationby filtering it through anhydrous sodium sulfate
  6. customevaporated to a yellow oil
  7. dissolutionThe oil was dissolved in chloroform
  8. customchromatographed (HPLC) on a silica gel column
  9. washeluted with a linear gradient
  10. customevaporated down

出典と根拠

ORDレコード
ord-ceb22f74969c48fe8b37535171125830
出典データセット
uspto-grants-2001_04
特許番号
US06221838B1

関連ノート

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