D-Phenylalanine → 3-(2-Bromophenyl)propionic acid

HRID 266035

反応式

HRID 266035 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.[Br-:17].[K+]>S(=O)(=O)(O)O>[CH:12]1[CH:13]=[C:8]([CH2:7][CH2:6][C:14]([OH:16])=[O:15])[C:9]([Br:17])=[CH:10][CH:11]=1

参加物

5

反応物 3

HCID 71567D-PhenylalanineHCID 253877Potassium BromideHCID 23668193Sodium Nitrite

生成物 1

HCID 3160103-(2-Bromophenyl)propionic acid収率 62%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

反応条件

温度
0 °C

実験手順

Sodium nitrite (10.3 g, 280 mmol) was added to a solution of D-phenylalanine (30.0 g, 181 mmol) and potassium bromide (73.5 g) in sulfuric acid (2.5N, 365 ml) over a period of one hour while maintaining the temperature of the reaction mixture at 0° C. The mixture was stirred for an additional hour at 0° C. and then for one hour at room temperature. The reaction solution was extracted with ether, the ether was back extracted with water, and the ether layer was dried over sodium sulfate. Ether was removed in vacuo, and distillation of the oily residue afforded 25.7 g of (R)-2-bromo-3-benzenepropanoic acid; b.p. 141° C. (0.55 mm of Hg); [α]D =+14.5° (c=2.4, chloroform).

後処理

  1. extractionThe reaction solution was extracted with ether
  2. extractionthe ether was back extracted with water
  3. dry with materialthe ether layer was dried over sodium sulfate
  4. customEther was removed in vacuo, and distillation of the oily residue

出典と根拠

ORDレコード
ord-a9c7661f29dc43ce8ac5440c0f49aeec
出典データセット
uspto-grants-1997_07
特許番号
US05650408

関連ノート

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