Trifluoroacetic acid → (2S,3S)-2-amino-N-(4-bromo-2-chloro-phenyl)-3-phenyl-butyramide

HRID 1433748

反応式

HRID 1433748 の反応式
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([Cl:9])[CH:3]=1.C(OC([NH:17][C@@H:18]([C@H:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH3:23])[C:19](O)=[O:20])=O)(C)(C)C.O(Cl)Cl.FC(F)(F)C(O)=O>N1C=CC=CC=1>[NH2:17][C@@H:18]([C@H:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH3:23])[C:19]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([Br:1])=[CH:3][C:4]=1[Cl:9])=[O:20]

参加物

6

反応物 4

HCID 6422Trifluoroacetic acidHCID 24646Chlorine monoxideHCID 6101694-Bromo-2-chloroanilineHCID 7021178(2S,3S)-2-((tert-Butoxycarbonyl)amino)-3-phenylbutanoic acid

生成物 1

HCID 69009703(2S,3S)-2-amino-N-(4-bromo-2-chloro-phenyl)-3-phenyl-butyramide収率 55.9%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
-20 °C

実験手順

4-Bromo-2-chloro-aniline (325 mg, 1.58 mmol) and (S,S)-2-tert-butoxycarbonylamino-3-phenyl-butyric acid (440 mg, 1.58 mmol) in pyridine (5 mL) were cooled to −30° C. Phosporus oxychloride (0.158 mL, 1.7 mmol) was added and stirred at −20° C. for 2 hours. The mixture was poured into ice water and extracted with ethyl acetate (3×). The combined organic extracts were washed with water, brine, dried over sodium sulfate and concentrated in vacuo. The residue was dissolved in dichloromethane (5 mL) at 0° C. and trifluoroacetic acid (3 mol) added. Stirring was continued for 2 hours at 0° C. The mixture was evaporated and the residue dissolved in ether. The ether solution was basified with saturated aqueous sodium bicarbonate and extracted with ether. The organic extracts were washed with brine, dried over sodium sulfate and evaporated to give (2S,3S)-2-amino-N-(4-bromo-2-chloro-phenyl)-3-phenyl-butyramide (325 mg, 55%).

後処理

  1. extractionextracted with ethyl acetate (3×)
  2. washThe combined organic extracts were washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in dichloromethane (5 mL) at 0° C.
  6. stirringStirring
  7. waitwas continued for 2 hours at 0° C
  8. customThe mixture was evaporated
  9. dissolutionthe residue dissolved in ether
  10. extractionextracted with ether
  11. washThe organic extracts were washed with brine
  12. dry with materialdried over sodium sulfate
  13. customevaporated

出典と根拠

ORDレコード
ord-0c55c916f03d40cbb741710fd867c04b
出典データセット
uspto-grants-2009_11
特許番号
US07612212B2

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