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

HRID 1698769

反応式

HRID 1698769 の反応式
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]

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%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-19f5d793898a4c83b763ac3eed7429f5
出典データセット
uspto-grants-2002_02
特許番号
US06344452B1

関連ノート

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