Acetic Acid → 2-Methoxyethyl 3-{[3-(trifluoromethyl)phenyl]amino}-2-butenoate

HRID 639156ノート

反応式

HRID 639156 の反応式
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6](=[O:11])[CH2:7][C:8](=O)[CH3:9].[F:12][C:13]([F:22])([F:21])[C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17].C(O)(=O)C>C1C=CC=CC=1>[F:12][C:13]([F:21])([F:22])[C:14]1[CH:15]=[C:16]([NH:17][C:8]([CH3:9])=[CH:7][C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[O:11])[CH:18]=[CH:19][CH:20]=1

参加物

5

反応物 3

HCID 176Acetic AcidHCID 73753-(Trifluoromethyl)anilineHCID 897342-Methoxyethyl acetoacetate

生成物 1

HCID 684267042-Methoxyethyl 3-{[3-(trifluoromethyl)phenyl]amino}-2-butenoate

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

To a solution of 4.81 g (30 mmol) 2-methoxyethyl-3-oxobutanoate in 90 ml benzene are added 4.83 g (30 mmol) 3-(trifluoromethyl)aniline and 1.80 g (30 mmol) acetic acid. The mixture is stirred under reflux for four hours using a Dean-Stark trap to remove water. After removal of the solvent in vacuo, the residue is purified by preparative HPLC (column: YMC C18 ODS-AQ 250 mm×30 mm, 11 μm; solvent A: acetonitrile, solvent B: water; gradient: 0 min 10% A, 3 min 10% A, 11 min 90% A, 13 min 90% A, 13.2 min 10% A, 15 min 10% A; wavelength: 220 nm; injection volume: ca. 900 μl ethanol solution; number of injections: 9). The product containing fractions are combined and concentrated in vacuo.

後処理

  1. temperatureunder reflux for four hours
  2. customto remove water
  3. customAfter removal of the solvent in vacuo
  4. customthe residue is purified by preparative HPLC (column: YMC C18 ODS-AQ 250 mm×30 mm, 11 μm; solvent A: acetonitrile, solvent B: water; gradient: 0 min 10% A, 3 min 10% A, 11 min 90% A, 13 min 90% A, 13.2 min 10% A, 15 min 10% A; wavelength: 220 nm; injection volume: ca. 900 μl ethanol solution; number of injections: 9)
  5. additionThe product containing fractions
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f707971a31294d07920c0c78028673e8
出典データセット
uspto-grants-2010_04
特許番号
US07691854B2

反応ノート

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