HCID 178471895, 화합물 → ethyl 2-[2-amino-5-(difluoromethoxy)-3,4,6-trifluorobenzoyl]-3-(cyclopropylamino)prop-2-enoate

HRID 2226495노트

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HRID 2226495 반응식
[CH:1]1([NH:4][CH:5]=[C:6]([C:12](=[O:29])[C:13]2[C:18]([N+:19]([O-])=O)=[C:17]([F:22])[C:16]([F:23])=[C:15]([O:24][CH:25]([F:27])[F:26])[C:14]=2[F:28])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1>C(O)C>[CH:1]1([NH:4][CH:5]=[C:6]([C:12](=[O:29])[C:13]2[C:18]([NH2:19])=[C:17]([F:22])[C:16]([F:23])=[C:15]([O:24][CH:25]([F:26])[F:27])[C:14]=2[F:28])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1

참가 물질

3

반응물 1

HCID 178471895HCID 178471895, 화합물

생성물 1

HCID 178471897ethyl 2-[2-amino-5-(difluoromethoxy)-3,4,6-trifluorobenzoyl]-3-(cyclopropylamino)prop-2-enoate수율 80.6%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

33.63 g (0.079 mole) of ethyl 3-cyclopropylamino-2-(3-difluoromethoxy-2,4,5-trifluoro-6-nitrobenzoyl)acrylate [(XIXa): X=X'=F, R1 =OCHF2, R17 =C2H5 ] were dissolved in 1300 ml of ethanol with heating. A stream of hydrogen was then bubbled through the solution in the presence of 8.4 g of 5% w/w palladium-on-carbon at room temperature for 40 minutes, whilst stirring. At the end of this time, the reaction mixture was filtered, and the filtrate was concentrated by evaporation under reduced pressure. The resulting residue was then purified by silica gel column chromatography using a 9:1 by volume mixture of toluene and ethyl acetate as the eluent, to give 25.1 g of ethyl 3-cyclopropylamino-2-(6-amino-3-difluoromethoxy-2,4,5-trifluorobenzoyl)acrylate [(XIXb): X=X'=F, R1 =OCHF2, R17 =C2H5 ] as a pale yellow powder, melting at 103°-104° C.

후처리

  1. temperaturewith heating
  2. customA stream of hydrogen was then bubbled through the solution in the presence of 8.4 g of 5% w/w palladium-on-carbon at room temperature for 40 minutes
  3. filtrationAt the end of this time, the reaction mixture was filtered
  4. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  5. customThe resulting residue was then purified by silica gel column chromatography
  6. additionby volume mixture of toluene and ethyl acetate as the eluent

출처 및 근거

ORD 기록
ord-cb01038227fb416290814f240cd74d39
출처 데이터셋
uspto-grants-1994_09
특허 번호
US05348961

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