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

HRID 1979462ノート

反応式

HRID 1979462 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 54512598(R)-2-((tert-Butoxycarbonyl)amino)-3-((2-nitrophenyl)amino)propanoic acid収率 99.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

(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%).

後処理

  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

出典と根拠

ORDレコード
ord-d6acb56ecc9e4e9eaee6e411c24b7b16
出典データセット
uspto-grants-2001_05
特許番号
US06239131B1

反応ノート

読み込み中…