Toluene → (2S)-2-bromo-3-phenylpropanoic acid

HRID 343041

반응식

HRID 343041 반응식
N[C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Br-:13].[K+].N([O-])=O.[Na+].C1(C)C=CC=CC=1>S(=O)(=O)(O)O.C(O)(=O)C>[Br:13][C@@H:2]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:10]([OH:12])=[O:11]

참가 물질

7

반응물 4

HCID 1140TolueneHCID 6140L-PhenylalanineHCID 253877Potassium BromideHCID 23668193Sodium Nitrite

생성물 1

HCID 9816009(2S)-2-bromo-3-phenylpropanoic acid

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 1118Sulfuric Acid용매

실험 절차

A solution of L-phenylalanine (30.0 g., 0.175 mole) and potassium bromide (73.5 g., 0.618 mole) in 2.5N sulfuric acid (365 ml.) was cooled down to 0° (ice-salt bath) and treated portionwise with sodium nitrite (19.3 g., 0.28 mole) over a period of 1.0 hour. Stirring was continued for 1.0 hour at 0° and at room temperature for 1.0 hour after which the reaction mixture was extracted with ether (3×250 ml.). The combined organic extracts were washed with water (100 ml.) and brine (50 ml.), dried (anhydrous magnesium sulfate), filtered, evaporated to dryness and dried in vacuo to give 34.46 g., of product; Rf =0.45 (toluene:acetic acid, 95:5).

후처리

  1. extractionafter which the reaction mixture was extracted with ether (3×250 ml.)
  2. washThe combined organic extracts were washed with water (100 ml.) and brine (50 ml.)
  3. dry with materialdried (anhydrous magnesium sulfate)
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customdried in vacuo
  7. customto give 34.46 g

출처 및 근거

ORD 기록
ord-3d9ca0e36a1147dcb1f0076bf196d42f
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05859239

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