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Acetic Anhydride → N-Formyl-2-phenylalanine

HRID 605412
ノート
印刷プレビュー

反応式

HRID 605412 の反応式
[NH2:1][C:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:6])[C:3]([OH:5])=[O:4].[C:13](OC(=O)C)(=[O:15])C>C(O)=O>[CH:13]([NH:1][C:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:6])[C:3]([OH:5])=[O:4])=[O:15]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 7918Acetic AnhydrideHCID 317222-Amino-2-phenylpropanoic acid

生成物 1

HCID 281276N-Formyl-2-phenylalanine

試薬・触媒・溶媒 1

HCID 284Formic Acid溶媒

実験手順

(RS)-2-amino-2-phenylpropanoic acid (20 g, 0.12 mol) in 88% formic acid (220 mL) was reacted with acetic anhydride (100 mL) at such rate as to keep the internal temperature at 60-65° C. After the final addition, the reaction was stirred until the internal temperature dropped to 35° C., and then concentrated. The solid residue was dried by azeotroping with toluene. The solid residue was dissolved in hot ethanol (70 mL), treated with active charcoal (0.5 g), and filtered. Hot water (210 mL) was added with stirring to the hot filtrate. The mixture was cooled in the refrigerator for 3 days. The resulting crystals was collected by filtration, washed with cold EtOH/water (1:3), and dried at 60° C. for 4 hours to give the title compound as colorless crystal. (17.8 g, 76%).

後処理

  1. customat 60-65° C
  2. additionAfter the final addition
  3. additiondropped to 35° C.
  4. concentrationconcentrated
  5. customThe solid residue was dried
  6. customby azeotroping with toluene
  7. dissolutionThe solid residue was dissolved in hot ethanol (70 mL)
  8. additiontreated with active charcoal (0.5 g)
  9. filtrationfiltered
  10. additionHot water (210 mL) was added
  11. stirringwith stirring to the hot filtrate
  12. temperatureThe mixture was cooled in the refrigerator for 3 days
  13. filtrationThe resulting crystals was collected by filtration
  14. washwashed with cold EtOH/water (1:3)
  15. customdried at 60° C. for 4 hours

出典と根拠

ORDレコード
ord-47153df84eb14fa6a7183ba7bf6b9ae7
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07910595B2

反応ノート

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