Triethylamine → Cyclopropanecarboxylic acid {2-[4-(tert-butyldimethylsilyloxy)phenyl]ethyl}[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amide

HRID 1434153노트

반응식

HRID 1434153 반응식
COC1C=CC(C2C[CH2:27][C:26]3C(=CC=[C:24]([O:29]C)[CH:25]=3)C2)=C(NCCC2C=CC(O)=CC=2)C=1.[Si:31]([O:38][C:39]1[CH:44]=[CH:43][C:42]([CH2:45][CH2:46][NH:47][C:48]2[CH:53]=[C:52]([O:54][CH3:55])[CH:51]=[CH:50][C:49]=2[CH:56]2[CH2:65][CH2:64][C:63]3[C:58](=[CH:59][CH:60]=[C:61]([O:66][CH3:67])[CH:62]=3)[CH2:57]2)=[CH:41][CH:40]=1)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32].C(N(CC)CC)C.C1(C(Cl)=O)CC1>O1CCCC1>[Si:31]([O:38][C:39]1[CH:40]=[CH:41][C:42]([CH2:45][CH2:46][N:47]([C:48]2[CH:53]=[C:52]([O:54][CH3:55])[CH:51]=[CH:50][C:49]=2[CH:56]2[CH2:65][CH2:64][C:63]3[C:58](=[CH:59][CH:60]=[C:61]([O:66][CH3:67])[CH:62]=3)[CH2:57]2)[C:24]([CH:25]2[CH2:26][CH2:27]2)=[O:29])=[CH:43][CH:44]=1)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 579340414-{2-[5-Methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenylamino]ethyl}phenolHCID 66625834{2-[4-(Tert-butyldimethylsilyloxy)phenyl]ethyl}[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amine

생성물 1

HCID 57933985Cyclopropanecarboxylic acid {2-[4-(tert-butyldimethylsilyloxy)phenyl]ethyl}[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Synthesized from 4-{2-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenylamino]ethyl}phenol according to an analogous synthetic method to Example 201, to a solution of the resulting {2-[4-(tert-butyldimethylsilyloxy)phenyl]ethyl}[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amine (2.3 g) in tetrahydrofuran (50 ml) was added triethylamine (895 mg), cyclopropanecarbonyl chloride (693 mg) was added dropwise thereto on an ice bath followed by stirring for 30 minutes at room temperature. The solution was extracted with ethyl acetate, then sequentially washed with a saturated aqueous solution of sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (2.3 g).

후처리

  1. additionwas added dropwise
  2. customon an ice bath followed
  3. extractionThe solution was extracted with ethyl acetate
  4. washsequentially washed with a saturated aqueous solution of sodium bicarbonate and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate system)

출처 및 근거

ORD 기록
ord-387b3f7ecb6e4b609d59efe57fb8a30d
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612114B2

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