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

HRID 1979462노트

반응식

HRID 1979462 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:13][NH2:14])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].F[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N+:28]([O-:30])=[O:29]>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:13][NH:14][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N+:28]([O-:30])=[O:29])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

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 99.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

(R)-2-tert-Butoxycarbonylamino-3-aminopropionic acid (5 g) and potassium carbonate (6.77 g) were added to a solution of 2-fluoronitrobenzene (3.45 g) in N,N-dimethylformamide (60 ml), and the mixture was stirred overnight at 70° C. After the reaction mixture was allowed to cool, the reaction mixture was poured into ice-water and washed with ethyl acetate. The water layer was adjusted to pH 3 with 1N hydrochloric acid, extracted with ethyl acetate. This organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. Hexane was added to the residue for crystallization, collected by filtration,to thereby obtain 7.9 g of the title compound (Yield 99%).

후처리

  1. temperatureto cool
  2. washwashed with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. washThis organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. additionHexane was added to the residue for crystallization
  8. filtrationcollected by filtration,to

출처 및 근거

ORD 기록
ord-d6acb56ecc9e4e9eaee6e411c24b7b16
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06239131B1

반응 노트

불러오는 중…