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Water → (R,E)-Ethyl 2-(N-(4-cyano-1-phenylbut-3-en-2-yl)-2-(trifluoromethoxy)phenylsulfonamido)acetate

HRID 1429409
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HRID 1429409 반응식
[C:1](/[CH:3]=[CH:4]/[C@H:5]([NH:13][S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][C:24]([F:27])([F:26])[F:25])(=[O:16])=[O:15])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)#[N:2].Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[C:1](/[CH:3]=[CH:4]/[C@H:5]([N:13]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][C:24]([F:25])([F:26])[F:27])(=[O:15])=[O:16])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)#[N:2]
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참가 물질

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반응물 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 71269687(R,E)-N-(4-Cyano-1-phenylbut-3-en-2-yl)-2-(trifluoromethoxy)benzenesulfonamide

생성물 1

HCID 71277869(R,E)-Ethyl 2-(N-(4-cyano-1-phenylbut-3-en-2-yl)-2-(trifluoromethoxy)phenylsulfonamido)acetate수율 73%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of compound 31g (4.2 g, 10.6 mmol) in DMF (100 mL) was added ethyl bromoacetate (2.1 g, 12.7 mmol) and K2CO3 (3.5 g, 25.4 mmol). The mixture was stirred at rt for 12 h, then water (100 mL) was added to the mixture. The mixture was extracted with EA three times and the combined organic layer was washed with brine and dried over anhydrous Na2SO4. After filtration, the filtrate was evaporated and the residue was purified by CC (hexane/EA=5:1) to give compound 31h (3.7 g, 73% yield).

후처리

  1. extractionThe mixture was extracted with EA three times
  2. washthe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationAfter filtration
  5. customthe filtrate was evaporated
  6. customthe residue was purified by CC (hexane/EA=5:1)

출처 및 근거

ORD 기록
ord-1f005715df5243969acff34ea0290f5b
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08940722B2

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