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

HRID 916174ノート

反応式

HRID 916174 の反応式
[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

参加物

5

反応物 3

HCID 867Malonic AcidHCID 707414-BromobenzaldehydeHCID 517165Ammonium Acetate

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-47878775ca3d45daa129ea7bfe917422
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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