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Ethyl Acetate → Tert-butyl 3-(4-carbamoyl-3-fluorophenylamino)-2-(4-(hydroxymethyl)phenyl)-3-oxopropylcarbamate

HRID 1944179
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HRID 1944179 반응식
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:40])[CH:12]([C:22]2[CH:27]=[CH:26][C:25]([CH2:28][O:29][Si](C(C)C)(C(C)C)C(C)C)=[CH:24][CH:23]=2)[CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:6][C:5]=1[F:41])(=[O:3])[NH2:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-].CCOC(C)=O>C1COCC1>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:40])[CH:12]([C:22]2[CH:23]=[CH:24][C:25]([CH2:28][OH:29])=[CH:26][CH:27]=2)[CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:6][C:5]=1[F:41])(=[O:3])[NH2:2]
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참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 59563790Tert-butyl 3-(4-carbamoyl-3-fluorophenylamino)-3-oxo-2-(4-((triisopropylsilyloxy)methyl)phenyl)propylcarbamate

생성물 1

HCID 59563726Tert-butyl 3-(4-carbamoyl-3-fluorophenylamino)-2-(4-(hydroxymethyl)phenyl)-3-oxopropylcarbamate

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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온도
0 °C

실험 절차

To tert-butyl 3-(4-carbamoyl-3-fluorophenylamino)-3-oxo-2-(4-((thisopropylsilyloxy)methyl)phenyl)propylcarbamate (E337) in THF under N2 at 0° C. was added TBAF, and the solution was stirred for 30 min at 0° C. The reaction was warmed to room temperature and stirred another 3.5 h. The compound was poured into EtOAc and washed with NH4Cl(sat), dried (MgSO4), filtered, and evaporated. Column chromatography (SiO2, 0-20% MeOH/CH2Cl2 gradient) gave pure tert-butyl 3-(4-carbamoyl-3-fluorophenylamino)-2-(4-(hydroxymethyl)phenyl)-3-oxopropylcarbamate (E337-1)

후처리

  1. temperatureThe reaction was warmed to room temperature
  2. stirringstirred another 3.5 h
  3. washwashed with NH4Cl(sat)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

출처 및 근거

ORD 기록
ord-7a9e39a5f254438ea2b2d34ea5db69a4
출처 데이터셋
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08394826B2

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