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

HRID 10915

반응식

HRID 10915 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.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]

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 6140L-PhenylalanineHCID 23668193Sodium Nitrite

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매2회

반응 조건

온도
20 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-420957afd9b44a9fab3ce48480a6b208
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094926B2

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