3,5-Difluoro-L-phenylalanine → HCID 68510986, compound

HRID 1713629Notes

Reaction equation

HRID 1713629 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([F:14])[CH:13]=1)[CH2:5][C@@H:6]([C:8]([OH:10])=[O:9])N.N([O-])=[O:16].[Na+]>OS(O)(=O)=O.O>[F:1][C:2]1[CH:3]=[C:4]([CH2:5][C@H:6]([OH:16])[C:8]([OH:10])=[O:9])[CH:11]=[C:12]([F:14])[CH:13]=1

Participants

5

Reactant 2

HCID 7163073,5-Difluoro-L-phenylalanineHCID 23668193Sodium Nitrite

Product 1

HCID 68510986HCID 68510986, compoundYield 74.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 1.6 g of (S)-3,5-difluoro-phenyalanine in 5.3 ml of H2SO4 (2.5N) is admixed dropwise at 0° C. with a solution of 0.829 g of sodium nitrite in 4.2 ml of H2O. The reaction mixture is stirred for 2 hours at 0° C. and then for 17 hours at ambient temperature. The reaction mixture is extracted with 2×100 ml of AcOEt. The combined organic phases are washed with 100 ml of saturated NaCl solution in H2O. Drying gives 1.197 g of yellow crystals. The acid obtained is used without further purification in the following step.

Workup

  1. waitfor 17 hours at ambient temperature
  2. extractionThe reaction mixture is extracted with 2×100 ml of AcOEt
  3. washThe combined organic phases are washed with 100 ml of saturated NaCl solution in H2O
  4. customDrying

Sources & evidence

ORD record
ord-a2d607dfff434bcb8b71120412f3aa4c
Source dataset
uspto-grants-2010_09
Patent number
US07795289B2

Reaction notes

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