Hydrogen Sulfide → HCID 67642491, compound

HRID 726897Notes

Reaction equation

HRID 726897 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C@@H:5]([C:7]([OH:9])=[O:8])[NH2:6].[OH-].[Na+].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.S>O>[CH2:12]([O:8][C:7](=[O:9])[C@H:5]([CH2:4][CH2:3][CH2:2][OH:1])[NH2:6])[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 52875876152-89-2

Product 1

HCID 67642491HCID 67642491, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Dissolve 5-hydroxynorvaline (13.3 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-hydroxynorvaline.

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-e6c43049d24241d48756ae874ca26394
Source dataset
uspto-grants-1998_01
Patent number
US05710324

Reaction notes

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