Potassium Carbonate → (R)-2-((tert-Butoxycarbonyl)amino)-3-((2-nitrophenyl)amino)propanoic acid

HRID 1698769

반응식

HRID 1698769 반응식
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[C:11]([O:15][C:16]([NH:18][C@H:19]([CH2:23][NH2:24])[C:20]([OH:22])=[O:21])=[O:17])([CH3:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:11]([O:15][C:16]([NH:18][C@H:19]([CH2:23][NH:24][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9])[C:20]([OH:22])=[O:21])=[O:17])([CH3:14])([CH3:13])[CH3:12]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 70209843-Amino-N-(tert-butoxycarbonyl)-D-alanine

생성물 1

HCID 54512598(R)-2-((tert-Butoxycarbonyl)amino)-3-((2-nitrophenyl)amino)propanoic acid수율 99%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

To a solution of 2-fluoronitrobenzene (3.45 g) in N,N-dimethylformamide (60 mL), (R)-(−)-2-tert-butoxycarbonylamino-3-amino-propionic acid (5 g) and potassium carbonate (6.77 g) were added, followed by stirring overnight at 70° C. The reaction mixture was allowed to cool down, poured into ice water, and then extracted with ethyl acetate. After 1 N hydrochloric acid was added to the aqueous layer to adjust pH to 3, the aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was then evaporated under reduced pressure. n-Hexane was added to the residue to for crystallization. The resultant crystals were collected by filtration, whereby the title compound (7.9 g) was obtained. Yield: 99%.

후처리

  1. temperatureto cool down
  2. extractionextracted with ethyl acetate
  3. additionAfter 1 N hydrochloric acid was added to the aqueous layer
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was then evaporated under reduced pressure
  8. additionn-Hexane was added to the residue to for crystallization
  9. filtrationThe resultant crystals were collected by filtration, whereby the title compound (7.9 g)
  10. customwas obtained

출처 및 근거

ORD 기록
ord-19f5d793898a4c83b763ac3eed7429f5
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06344452B1

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