Glycine → HCID 54347809, compound

HRID 1493624Notes

Reaction equation

HRID 1493624 reaction equation
[NH2:1]CC(O)=O.[CH3:6][O:7][C:8](=[O:19])[CH2:9][NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][F:18])[CH:12]=1.N([O-])=O.[Na+]>C(O)(=O)C.O.[Zn]>[F:18][CH2:17][C:13]1[CH:12]=[C:11]([N:10]([CH2:9][C:8]([O:7][CH3:6])=[O:19])[NH2:1])[CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 750Glycine2×HCID 19829895N-[3-(Fluoromethyl)phenyl]glycine methyl esterHCID 23668193Sodium Nitrite

Product 1

HCID 54347809HCID 54347809, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent3×

Procedure

The glycine (Intermediate 54, 1 g, 5.1 mmol) was dissolved in acetic acid (10 ml) and water (1 ml) and cooled to ~5° C. Sodium nitrite (0.37 g, 5.4 mmol) in water (1.3 ml) was added to the glycine solution dropwise, maintaining the temperature at or below 5° C. The reaction was stirred at this temperature for 1 h. Zinc (1.33 g, 20.3 mmol) was then added slowly to the reaction keeping the temperature below 4° C., and the reaction was stirred for 1 h. The reaction mixture was poured into water (100 ml) and extracted with ethyl acetate (3×100 ml). The combined organic extracts were washed with water (2×100 ml) followed by saturated aqueous sodium bicarbonate (1×100 ml) then water (100 ml), dried (Na2SO4) and concentrated in vacuo to give an orange oil (1.06 g). The crude material was purified by chromatography on silica (Merck 9385, 28 g) eluted with ether-hexane 1:4 to give the title compound (Intermediate 55, 453 mg, 40%).

Workup

  1. temperaturemaintaining the temperature at or below 5° C
  2. customthe temperature below 4° C.
  3. stirringthe reaction was stirred for 1 h
  4. extractionextracted with ethyl acetate (3×100 ml)
  5. washThe combined organic extracts were washed with water (2×100 ml)
  6. dry with materialwater (100 ml), dried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-37e1d13e7f8b488aaca81823d0be978b
Source dataset
uspto-grants-1991_06
Patent number
US05023255

Reaction notes

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