3-(Trifluoromethyl)aniline → Benzyl 3-oxo-3-{[3-(trifluoromethyl)phenyl]amino}propanoate

HRID 641584

反応式

HRID 641584 の反応式
[C:1]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:6])[CH2:2][C:3]([O-:5])=O.CN1CCOCC1.P(Cl)(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O.[F:39][C:40]([F:49])([F:48])[C:41]1[CH:42]=[C:43]([NH2:47])[CH:44]=[CH:45][CH:46]=1>C1COCC1>[CH2:8]([O:7][C:1](=[O:6])[CH2:2][C:3]([NH:47][C:43]1[CH:44]=[CH:45][CH:46]=[C:41]([C:40]([F:39])([F:48])[F:49])[CH:42]=1)=[O:5])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

6

反応物 4

HCID 73753-(Trifluoromethyl)anilineHCID 79724-MethylmorpholineHCID 75654Diphenyl chlorophosphateHCID 22247814Benzyl malonate

生成物 1

HCID 59666221Benzyl 3-oxo-3-{[3-(trifluoromethyl)phenyl]amino}propanoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

mono-Benzyl malonate (10 g) was dissolved in THF (100 ml), 4-methylmorpholine and cooled to −22° C. prior to the slow addition of diphenyl chlorophosphate (14 ml) and 3-trifluoromethyl-phenylamine (19 ml). After the reaction was warmed to rt overnight, it was heated to gently reflux for 0.5 h. After the reaction was cooled to rt, the solid was filtered off. The filtrate was concentrated. EtOAc was added along with 1N HCl solution. The organic layer was washed with NaHCO3 solution (aq) and brine, dried (MgSO4), filtered, and concentrated. Flash chromatography of the resulting residue gave N-(3-trifluoromethyl-phenyl)-malonamic acid benzyl ester (8.0 g): 1H NMR (CDCl3, δppm, 300 mHz) 3.56 (s, 2H), 5.26 (s, 2H), 7.40 (m, 7H), 7.75 (d, 1H), 7.83 (s, 1H), 9.43 (s, br, 1H).

後処理

  1. temperatureit was heated
  2. temperatureto gently reflux for 0.5 h
  3. temperatureAfter the reaction was cooled to rt
  4. filtrationthe solid was filtered off
  5. concentrationThe filtrate was concentrated
  6. additionEtOAc was added along with 1N HCl solution
  7. washThe organic layer was washed with NaHCO3 solution (aq) and brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-05e0347d29644926bfb2ad1dffe84085
出典データセット
uspto-grants-2010_04
特許番号
US07696205B2

関連ノート

読み込み中…