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

HRID 233367

反応式

HRID 233367 の反応式
N([O-])=O.[Na+].N[C@@H:6]([C:14]([OH:16])=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[BrH:17].O>>[Br:17][C@H:6]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]([OH:16])=[O:15]

参加物

4

反応物 3

HCID 71567D-PhenylalanineHCID 22326455Hydrobromide monohydrateHCID 23668193Sodium Nitrite

生成物 1

HCID 11746403(R)-2-Bromo-3-phenylpropionic acid収率 60%

反応条件

温度
0 °C

実験手順

Sodium nitrite (27 g in water) is added at 0° C. to a solution of D-phenylalanine (40 g) in a mixture of 48% hydrobromic acid/water (1:1 by volume). The mixture is stirred for 30 minutes at 0° C. and then for 2 hours 30 minutes at a temperature close to 0° C. The reaction mixture is extracted with ether. The organic extracts are washed with water and a saturated sodium chloride solution and then dried over sodium sulphate. After filtration and concentration to dryness, the obtained residue is purified by distillation. (R)-2-Bromo-3-phenylpropanoic acid (33 g) is obtained which has the following characteristics: B.p.1kPa =154° C.; Rf =0.47 (methylene chloride/methanol). The yield is 60%.

後処理

  1. customfor 2 hours 30 minutes at a temperature close to 0° C
  2. extractionThe reaction mixture is extracted with ether
  3. washThe organic extracts are washed with water
  4. dry with materiala saturated sodium chloride solution and then dried over sodium sulphate
  5. filtrationAfter filtration and concentration to dryness
  6. distillationthe obtained residue is purified by distillation

出典と根拠

ORDレコード
ord-4bae0f07b45446fd86a1daabd50db09a
出典データセット
uspto-grants-1997_01
特許番号
US05591891

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