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

HRID 1440104ノート

反応式

HRID 1440104 の反応式
[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

参加物

3

反応物 1

HCID 178471895HCID 178471895、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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% 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.

後処理

  1. temperaturewith heating
  2. customA stream of hydrogen was then bubbled through the solution in the presence of 8.4 g of 5% 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

出典と根拠

ORDレコード
ord-3b3e78adf13e4ba18bb410a0a0e75276
出典データセット
uspto-grants-1996_03
特許番号
US05496951

反応ノート

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