Triethylamine → 2-(4-Chlorophenyl)-2-(trifluoroacetamido)acetic acid

HRID 1769310ノート

反応式

HRID 1769310 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]([OH:12])=[O:11])[NH2:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:20][C:21]([F:28])([F:27])[C:22](OCC)=[O:23]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:10]([OH:12])=[O:11])[NH:9][C:22](=[O:23])[C:21]([F:28])([F:27])[F:20])=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 9794Ethyl trifluoroacetateHCID 587821Benzeneacetic acid, alpha-amino-4-chloro-

生成物 1

HCID 199580242-(4-Chlorophenyl)-2-(trifluoroacetamido)acetic acid収率 46.8%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

A mixture of 2-(p-chlorophenyl)glycine (37.1 g, 0.2 mol) in methanol is treated with triethylamine (20.2 g, 0.2 mol), stirred for 10 minutes, treated dropwise with ethyl trifluoroacetate (35.5 g, 0.25 mol), stirred for 4 days, diluted with methanol and treated with Dowex 50×8-100 ion exchange resin. The reaction mixture is stirred for 10 minutes and filtered. The filter cake is washed with methanol. The filtrates are combined and concentrated in vacuo to afford a yellow solid which is recrystallized from 1,2-dichloroethane to give the title compound as white crystals, 26.4 g (46.8% yield), mp 170°-172° C.

後処理

  1. stirringstirred for 4 days
  2. additiontreated with Dowex 50×8-100 ion exchange resin
  3. stirringThe reaction mixture is stirred for 10 minutes
  4. filtrationfiltered
  5. washThe filter cake is washed with methanol
  6. concentrationconcentrated in vacuo
  7. customto afford a yellow solid which
  8. customis recrystallized from 1,2-dichloroethane

出典と根拠

ORDレコード
ord-4b6b155308e44524955befaf00e431e6
出典データセット
uspto-grants-1995_01
特許番号
US05380876

反応ノート

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