Sulfuric Acid → 3-Phenyllactic acid, (S)-

HRID 10915

反応式

HRID 10915 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.S(=O)(=O)(O)[OH:14].N([O-])=O.[Na+]>O>[OH:14][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

5

反応物 3

HCID 1118Sulfuric AcidHCID 6140L-PhenylalanineHCID 23668193Sodium Nitrite

生成物 1

HCID 4447183-Phenyllactic acid, (S)-収率 69%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
20 °C

実験手順

L-Phenylalanine (10.00 g, 60.5 mmol) was added to a dilution of 14.83 g (151.3 mmol) of concentrated sulfuric acid in 110 g of water and then, at an inside temperature of 20° C., a mixture of 10.45 g (151.5 mmol) of sodium nitrite and 20 g of water was added over 5 hours. After addition, the mixture was further stirred at 20° C. for 20 hours and, thereafter, the same work-up procedure as in Example 1 was followed. The combined extract (114.4 g) obtained contained 6.9 g of (2S)-2-hydroxy-3-phenylpropionic acid (yield 69%, optical purity 96.5% ee). The proton concentration (normality) in the reaction of this comparative example was 2.7 mol/kg, the amount of the protonic acid was 5.0 equivalents (relative to L-phenylalanine), and the reaction temperature was 20° C.

後処理

  1. additionwas added over 5 hours
  2. additionAfter addition
  3. extractionThe combined extract (114.4 g)
  4. customobtained

出典と根拠

ORDレコード
ord-420957afd9b44a9fab3ce48480a6b208
出典データセット
uspto-grants-2006_08
特許番号
US07094926B2

関連ノート

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