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

HRID 916175노트

반응식

HRID 916175 반응식
[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

참가 물질

5

반응물 3

HCID 867Malonic AcidHCID 680234-FluorobenzaldehydeHCID 517165Ammonium Acetate

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-aeb9d77789e44df3ab74d9a2e0f0dd6b
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07268164B2

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