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

HRID 325154

반응식

HRID 325154 반응식
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]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 54900Raloxifene HydrochlorideHCID 845041-Hexanesulfonyl chloride

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ceb22f74969c48fe8b37535171125830
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06221838B1

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