D-Phenylalanine → (R)-3-phenyllactic acid

HRID 373653Notes

Reaction equation

HRID 373653 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.N([O-])=[O:14].[Na+]>OS(O)(=O)=O.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 2

HCID 71567D-PhenylalanineHCID 23668193Sodium Nitrite

Product 1

HCID 643327(R)-3-phenyllactic acidYield 54.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

Following the procedure of Johnson, 1980, D-phenylalanine (16.5 g, 100 mmol) was dissolved in 1N H2SO4 (150 ml) and cooled to 0° C. A solution of NaNO2 (10.5 g, 150 mmol) in water (50 ml) was added dropwise. The mixture was stirred for 2 h at 0° C. and for 3 h at 25° C. The product was extracted into ether (5×100 ml) and the combined ether extracts were dried over Na2SO4 and concentrated in vacuo to about 100 ml. Hexane (300 ml) was added and the product which crystallized out was collected by vacuum filtration to afford the title compound as a colorless solid (9 g, 54%); mp=124°-125° C.

Workup

  1. extractionThe product was extracted into ether (5×100 ml)
  2. dry with materialthe combined ether extracts were dried over Na2SO4
  3. concentrationconcentrated in vacuo to about 100 ml
  4. additionHexane (300 ml) was added
  5. customthe product which crystallized out
  6. filtrationwas collected by vacuum filtration

Sources & evidence

ORD record
ord-af1e8730b5874164926edc2098a1e5a1
Source dataset
uspto-grants-1992_11
Patent number
US05164388

Reaction notes

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