Malonic Acid → 3-Amino-3-(4-fluorophenyl)propanoic acid

HRID 916175ノート

反応式

HRID 916175 の反応式
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([O-:13])(=[O:12])[CH3:11].[NH4+:14].C(O)(=O)CC(O)=O>C(O)C>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([CH2:11][C:10]([OH:13])=[O:12])[NH2:14])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 867Malonic AcidHCID 680234-FluorobenzaldehydeHCID 517165Ammonium Acetate

生成物 1

HCID 5798853-Amino-3-(4-fluorophenyl)propanoic acid収率 68.5%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

4-Fluorobenzaldehyde (10 g, 80 mmol), ammonium acetate (8.2487 g, 107 mmol) and malonic acid (8.3285 g, 80 mmol) were refluxed (slow) in absolute ethanol (60 mL) for 48 hours. White solid was filtered and purified by ethanol recrystallization to afford β-4-fluorophenyl-β-alanine (10.04 g, 54.8 mmol, 68.5%); MP: 216-217° C.; IR (KBr): 3160, 1606 cm−1; TLC: RF=0.41 (solvent 24), 0.42 (solvent 25); 1H NMR (D2O/K2CO3): δ 7.28-7.19 (m, 2H), 7.03-6.91 (m, 2H), 4.10 (t, J=7.39 Hz, 1H), 2.54-2.34 (m, 2H). Anal. Calcd for C9H10FNO2.5/3H2O: C, 50.70; H, 6.30; N, 6.57. Found: C, 50.34; H, 6.39; N, 6.30.

後処理

  1. filtrationWhite solid was filtered
  2. custompurified by ethanol recrystallization

出典と根拠

ORDレコード
ord-aeb9d77789e44df3ab74d9a2e0f0dd6b
出典データセット
uspto-grants-2007_09
特許番号
US07268164B2

反応ノート

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