Malonic Acid → (RS)-beta-Amino-beta-(4-bromophenyl)propionic acid

HRID 916174노트

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HRID 916174 반응식
[Br: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>[Br: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 707414-BromobenzaldehydeHCID 517165Ammonium Acetate

생성물 1

HCID 554034(RS)-beta-Amino-beta-(4-bromophenyl)propionic acid수율 34.2%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
70 °C

실험 절차

4-Bromobenzaldehyde (10 g, 54 mmol), ammonium acetate (8.663 g, 112.4 mmol) and malonic acid (5.6762 g, 54.5 mmol) were refluxed (slow) in absolute ethanol (45 mL) for 150 hours. White solid was filtered and dissolved into a warm (70° C.) solution of 50 mL of Na2CO3 and 50 mL of H2O. This solution was then extracted with 100 mL of diethyl ether three times. The aqueous layer was further acidified to pH 7 to produce white solid β-4-bromophenyl-β-alanine (4.5140 g, 18.49 mmol, 34.2%); MP: 234° C.; IR (KBr): 3061, 1594 cm−1; TLC: RF=0.35 (solvent 24), 0.32 (solvent 25); 1H NMR (D2O/K2CO3): δ 7.42-7.38 (m, 2H), 7.17-7.14 (m, 2H), 4.11-4.07 (t, J=7.25 Hz, 1H), 2.48-2.36 (m, 2H). Anal. Calcd for C9H10BrNO2: C, 44.29; H, 4.13; N, 5.74. Found: C, 44.35; H, 3.93; N, 5.70.

후처리

  1. filtrationWhite solid was filtered
  2. dissolutiondissolved into
  3. extractionThis solution was then extracted with 100 mL of diethyl ether three times

출처 및 근거

ORD 기록
ord-47878775ca3d45daa129ea7bfe917422
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07268164B2

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