Trifluoroacetic acid → HCID 69009703, 화합물

HRID 1433748

반응식

HRID 1433748 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 69009703HCID 69009703, 화합물수율 55.9%

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
-20 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-0c55c916f03d40cbb741710fd867c04b
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612212B2

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