Water → 3-Phenyllactic acid, (S)-

HRID 10922Notes

Reaction equation

HRID 10922 reaction equation
Cl.N[C@H:3]([C:11]([OH:13])=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.S(=O)(=O)(O)[OH:15].N([O-])=O.[Na+].O>C(OCC)C>[OH:15][C@@H:3]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:11]([OH:13])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 12000150L-Phenylalanine, hydrochloride (1:1)HCID 23668193Sodium Nitrite

Product 1

HCID 4447183-Phenyllactic acid, (S)-Yield 42%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

L-Phenylalanine hydrochloride (12.2 g, 60.5 mmol) was added to 183 ml of 5% sulfuric acid (sulfuric acid: 96.0 mmol) and the solution was treated with a mixture of 8.35 g (121 mmol) of sodium nitrite and 44.5 g of water at 0° C. for 3 hours. Thereafter, 100 ml of diethyl ether was added to the reaction mixture and, after stirring, the organic phase was separated (extract 1). Further, 50 ml of diethyl ether was added to the aqueous phase and, after stirring, the organic phase was separated (extract 2). The extracts 1 and 2 were combined. The combined extract (95.0 g) contained 4.2 g of (2S)-2-hydroxy-3-phenylpropionic acid (yield 42%, optical purity 92.6% ee). The proton concentration (normality) in the reaction of this comparative example was 1.4 mol/kg, the amount of the protonic acid was 4.0 equivalents (relative to L-phenylalanine), and the reaction temperature was 0° C.

Workup

  1. customthe organic phase was separated
  2. extraction(extract 1)
  3. additionFurther, 50 ml of diethyl ether was added to the aqueous phase
  4. stirringafter stirring
  5. customthe organic phase was separated
  6. extraction(extract 2)
  7. extractionThe combined extract (95.0 g)

Sources & evidence

ORD record
ord-79eb3b90098a49eca07b18af68982a22
Source dataset
uspto-grants-2006_08
Patent number
US07094926B2

Reaction notes

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