Hydrogen Sulfide → HCID 67643155, compound

HRID 1109024Notes

Reaction equation

HRID 1109024 reaction equation
[OH:1][CH2:2][CH:3]=[CH:4][CH:5]([NH2:9])[C:6]([OH:8])=[O:7].[OH-].[Na+].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.S>O>[CH2:12]([O:7][C:6](=[O:8])[CH:5]([NH2:9])[CH:4]=[CH:3][CH2:2][OH:1])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 402Hydrogen SulfideHCID 7498Benzyl BromideHCID 14798Sodium Hydroxide2×HCID 53860975HCID 53860975, compound

Product 1

HCID 67643155HCID 67643155, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Dissolve 5-hydroxy-2-amino-3-pentenoic acid (13.1 g, 0.1 mol) in 1N sodium hydroxide (200 mL, 0.2 mol). Add a solution of CuSO4.5H2O (12.5 g, 0.05 mol) in water (50 mL). Stir the mixture until solution is complete. Treat with benzyl bromide (17.1 g, 0.1 mol) and stir at room temperature until reaction is complete. Suction filter, wash the residue with 1:3.5 methanol-water and dry at 60° C. to give the copper complex. Suspend the copper complex in water, treat with excess hydrogen sulfide, heat to boiling, then cool to room temperature. Mix with 1N sodium hydroxide and filter. Stir the filtrate with a slight excess of 1N hydrochloric acid and filter. Wash the residue with water and dry to give O-benzyl-5-hydroxy-2-amino-3-pentenoic acid.

Workup

  1. stirringstir at room temperature until reaction
  2. filtrationSuction filter
  3. washwash the residue with 1:3.5 methanol-water
  4. customdry at 60° C.
  5. customto give the copper complex
  6. temperatureheat
  7. filtrationfilter
  8. stirringStir the filtrate with a slight excess of 1N hydrochloric acid
  9. filtrationfilter
  10. washWash the residue with water
  11. customdry

Sources & evidence

ORD record
ord-16fafba99d1244ac8e6b0bd9e5425ed2
Source dataset
uspto-grants-1994_06
Patent number
US05318992

Reaction notes

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