L-Phenylalanine → 3-Phenyllactic acid, (S)-

HRID 1886521Notes

Reaction equation

HRID 1886521 reaction equation
N([O-])=[O:2].[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>O.S(=O)(=O)(O)O>[OH:2][C@@H:6]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]([OH:16])=[O:15]

Participants

5

Reactant 2

HCID 6140L-PhenylalanineHCID 23668193Sodium Nitrite

Product 1

HCID 4447183-Phenyllactic acid, (S)-Yield 87.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
50 °C

Procedure

A solution of sodium nitrite (51.8 g, 720 mmol) in 200 mL of water was added dropwise over 6 hours to a stirred solution of L-phenylalanine (33.04 g, 200 mmol) in 500 mL of 10% sulfuric acid at 50° C. After the addition was complete, the reaction mixture was stirred for 3 hours at 50° C, then at room temperature overnight. The reaction mixture was extracted with ethyl acetate (3×200 mL, 2×100 mL), then the combined organic extract was washed with water and brine, dried over sodium sulfate and evaporated to yield 28.98 g of a yellow solid. Recrystallization from benzene afforded 22.15 g of the title A compound as white needles, m.p. 120°-124° C.

Workup

  1. additionAfter the addition
  2. customat room temperature
  3. customovernight
  4. extractionThe reaction mixture was extracted with ethyl acetate (3×200 mL, 2×100 mL)
  5. extractionthe combined organic extract
  6. washwas washed with water and brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-5c34e5420e7c418684e43e0f5b3d7569
Source dataset
uspto-grants-1992_09
Patent number
US05151513

Reaction notes

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