Triethylamine → HCID 59760055、化合物

HRID 1879120ノート

反応式

HRID 1879120 の反応式
C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[C:13]([C:14]([OH:16])=O)=[C:12]([F:17])[C:11]([O:18][CH3:19])=[CH:10][CH:9]=1.[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:23][CH:22]=1.C(N(CC)CC)C>ClCCl.CN(C)C=O.O>[CH2:31]([O:30][C:28](=[O:29])[CH2:27][C:24]1[CH:23]=[CH:22][C:21]([NH:20][C:14]([C:13]2[C:8]([Cl:7])=[CH:9][CH:10]=[C:11]([O:18][CH3:19])[C:12]=2[F:17])=[O:16])=[CH:26][CH:25]=1)[CH3:32]

参加物

8

反応物 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 225219p-Aminophenylacetic acid ethyl esterHCID 38560396-Chloro-2-fluoro-3-methoxybenzoic acid

生成物 1

HCID 59760055HCID 59760055、化合物収率 94.1%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

Oxalyl chloride (193 μl, 2.21 mmol) was added dropwise to a solution of 6-chloro-2-fluoro-3-(methyloxy)benzoic acid (300 mg, 1.47 mmol) in dichloromethane (5 ml). To this was added dimethylformamide (1 drop) and the reaction was stirred at room temperature for 3 hrs. The solvent was evaporated to afford a yellow semi-solid. This semi-solid was dissolved in dichloromethane (5 ml) and ethyl (4-aminophenyl)acetate (316 mg, 1.76 mmol) followed by triethylamine (287 μl, 2.06 mmol) were added. The resultant solution was stirred at room temperature overnight. The reaction was diluted with water and the phases separated. The organic layer was dried (Na2SO4), the solvent evaporated and the residue purified by flash chromatography (Biotage SP4, 25+M silica column, 0→50% ethyl acetate/petrol) to afford the title as a yellow semi-solid (506 mg, 94%). MS (ES+) m/z 366 [M+H+] (C18H1735ClFNO4).

後処理

  1. customThe solvent was evaporated
  2. customto afford a yellow semi-solid
  3. additionwere added
  4. customthe phases separated
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. customthe solvent evaporated
  7. customthe residue purified by flash chromatography (Biotage SP4, 25+M silica column, 0→50% ethyl acetate/petrol)

出典と根拠

ORDレコード
ord-25cb468d47474fd88cd11393199e1a9a
出典データセット
uspto-grants-2012_11
特許番号
US08314147B2

反応ノート

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