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

HRID 639155

반응식

HRID 639155 반응식
O=[C:2]([CH3:10])[CH2:3][C:4]([O:6][CH:7]([CH3:9])[CH3:8])=[O:5].[F:11][C:12]([F:21])([F:20])[C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=1)[NH2:16].C(O)(=O)C>C1C=CC=CC=1>[F:11][C:12]([F:20])([F:21])[C:13]1[CH:14]=[C:15]([NH:16][C:2]([CH3:10])=[CH:3][C:4]([O:6][CH:7]([CH3:9])[CH3:8])=[O:5])[CH:17]=[CH:18][CH:19]=1

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 73753-(Trifluoromethyl)anilineHCID 68329Isopropyl acetoacetate

생성물 1

HCID 68427757Isopropyl 3-{[3-(trifluoromethyl)phenyl]amino}-2-butenoate

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

To a solution of 4.33 g (30 mmol) isopropyl 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: 8). The product containing fractions are combined and concentrated in vacuo.

후처리

  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: 8)
  5. additionThe product containing fractions
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-ae36b9a8d359456384167377ce0e393f
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691854B2

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