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

HRID 10913

Reaction equation

HRID 10913 reaction equation
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]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6140L-PhenylalanineHCID 23668193Sodium Nitrite

Product 1

HCID 4447183-Phenyllactic acid, (S)-Yield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
20 °C

Procedure

L-Phenylalanine (10.00 g, 60.5 mmol) was added to a dilution of 5.93 g (60.5 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 (116.1 g) obtained contained 8.7 g of (2S)-2-hydroxy-3-phenylpropionic acid (yield 87%, optical purity 95.2% ee). The proton concentration (normality) in the reaction of this example was 1.1 mol/kg, the amount of the protonic acid was 2.0 equivalents (relative to L-phenylalanine), and the reaction temperature was 20° C.

Workup

  1. additionwas added over 5 hours
  2. additionAfter addition
  3. extractionThe combined extract (116.1 g)
  4. customobtained

Sources & evidence

ORD record
ord-edcb3a81fb514e78824e93b36d4fa57d
Source dataset
uspto-grants-2006_08
Patent number
US07094926B2

Linked notes

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