L-Phenylalanine → (+-)-3-Phenyllactic acid

HRID 229751Notes

Reaction equation

HRID 229751 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>[C:8]1([CH2:7][CH:6]([OH:2])[C:14]([OH:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 6140L-PhenylalanineHCID 23668193Sodium Nitrite

Product 1

HCID 3848(+-)-3-Phenyllactic acidYield 74.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 0.829 g of sodium nitrite in 4.2 ml of water is added dropwise at 0° C. to a suspension of 1.6 g of phenylalanine in 5.3 ml of sulphuric acid (2.5N). The reaction mixture is stirred for 2 hours at 0° C. and then for 17 hours at room temperature. The reaction mixture is extracted with twice 100 ml of ethyl acetate. The pooled organic phases are washed with 100 ml of a saturated sodium chloride solution in water. 1.2 g of yellow crystals are obtained after drying.

Workup

  1. waitfor 17 hours at room temperature
  2. extractionThe reaction mixture is extracted with twice 100 ml of ethyl acetate
  3. washThe pooled organic phases are washed with 100 ml of a saturated sodium chloride solution in water

Sources & evidence

ORD record
ord-5e14149ae8974f1bb041da403f659096
Source dataset
uspto-grants-2009_07
Patent number
US07563903B2

Reaction notes

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