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

HRID 1189

反応式

HRID 1189 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 1118Sulfuric Acid溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-89c19946194d4a158a9cbb1375586293
出典データセット
uspto-grants-1998_03
特許番号
US05723457

関連ノート

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