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

HRID 585089ノート

反応式

HRID 585089 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-5015f08117b345f8a15c6f310c74c613
出典データセット
uspto-grants-2005_08
特許番号
US06930112B2

反応ノート

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