D-Phenylalanine → (R)-2-Bromo-3-phenylpropionic acid

HRID 902905

反応式

HRID 902905 の反応式
[Br-:1].[K+].N[C@@H:4]([C:12]([OH:14])=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.N([O-])=O.[Na+]>S(=O)(=O)(O)O>[Br:1][C@H:4]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:12]([OH:14])=[O:13]

参加物

5

反応物 3

HCID 71567D-PhenylalanineHCID 253877Potassium BromideHCID 23668193Sodium Nitrite

生成物 1

HCID 11746403(R)-2-Bromo-3-phenylpropionic acid収率 51.9%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

反応条件

温度
0 °C

実験手順

Potassium bromide (24.49 g, 0.21 moles) was first dissolved in a 2.50 N aqueous solution of sulfuric acid (120 mL). To this stirring solution was then added D-phenylalanine (10.00 g, 60.54 mmoles). After the addition, the mixture was cooled down to 0° C. and sodium nitrite (6.27 g., 90.87 mmoles) was added in small portions during 30 minutes. A strong bubbling was observed. The reaction was kept at this temperature for 50 minutes, and it was then allowed to proceed at room temperature for another 60 minutes. The crude product was isolated using standard work up and the obtained residue was purified by flash chromatography (SiO2, 30% ethyl acetate-70% hexanes) to give 7.20 g (51.9% yield) of the title compound as a yellowish oil: 1H NMR (CDCl3, 300 MHz) □ 10.86 (br s, 1H), 7.31 (m, 5H), 4.48 (t, 1H), 3.51 (dd, 1H), 3.29 (dd, 1H); 13C NMR (CDCl3, 75 MHz) □175.29, 136.26, 129.10, 128.69, 127.42, 44.83, 40.62.

後処理

  1. additionAfter the addition
  2. customA strong bubbling
  3. waitto proceed at room temperature for another 60 minutes
  4. customThe crude product was isolated
  5. customthe obtained residue was purified by flash chromatography (SiO2, 30% ethyl acetate-70% hexanes)

出典と根拠

ORDレコード
ord-7032ca5b14e5440d92c258596283f81f
出典データセット
uspto-grants-2008_04
特許番号
US07365091B2

関連ノート

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