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

HRID 233367

반응식

HRID 233367 반응식
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]

참가 물질

4

반응물 3

HCID 71567D-PhenylalanineHCID 22326455Hydrobromide monohydrateHCID 23668193Sodium Nitrite

생성물 1

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

반응 조건

온도
0 °C

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-4bae0f07b45446fd86a1daabd50db09a
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05591891

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