Ethyl Methacrylate → HCID 86747055, compound

HRID 2253573Notes

Reaction equation

HRID 2253573 reaction equation
[NH2:1][C@@H:2]([CH2:6][CH2:7][C:8]([NH:10][C@H:11]([C:14]([NH:16][CH2:17][C:18]([OH:20])=[O:19])=[O:15])[CH2:12][SH:13])=[O:9])[C:3]([OH:5])=[O:4].[OH-].[Na+].[C:23]([O:28][CH2:29][CH3:30])(=[O:27])[C:24]([CH3:26])=[CH2:25]>O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:23]([CH:24]([CH3:26])[CH2:25][S:13][CH2:12][C@@H:11]([C:14]([NH:16][CH2:17][C:18]([OH:20])=[O:19])=[O:15])[NH:10][C:8](=[O:9])[CH2:7][CH2:6][C@@H:2]([C:3]([OH:5])=[O:4])[NH2:1])([O:28][CH2:29][CH3:30])=[O:27]

Participants

6

Reactant 3

HCID 7343Ethyl MethacrylateHCID 14798Sodium HydroxideHCID 124886Glutathione

Product 1

HCID 86747055HCID 86747055, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 962WaterSolvent

Procedure

In 100 ml of water is dissolved 6.2 g of glutathione and the solution is adjusted to pH 7 with 2N-sodium hydroxide. To this solution is added 4 ml of ethyl methacrylate and the mixture is stirred at room temperature for 48 hours. Thereafter, 4.4 g of copper acetate is added and dissolved and the precipitated copper salt is collected by filtration and rinsed with water. This copper salt is suspended in 150 ml of water and hydrogen sulfide is bubbled through the suspension with stirring to precipitate the copper sulfide. This copper sulfide is filtered off and the filtrate is concentrated. The resulting white crystals are recovered by filtration and recrystallized from water to give 4.5 g of needlets melting at 193°-194° C. (decompn.) TLC, silica gel Rf=0.28 (n-butanol-acetic acid-water=4:1:1)

Workup

  1. dissolutiondissolved
  2. filtrationthe precipitated copper salt is collected by filtration
  3. washrinsed with water
  4. customhydrogen sulfide is bubbled through the suspension
  5. stirringwith stirring
  6. customto precipitate the copper sulfide
  7. filtrationThis copper sulfide is filtered off
  8. concentrationthe filtrate is concentrated
  9. filtrationThe resulting white crystals are recovered by filtration
  10. customrecrystallized from water
  11. customto give 4.5 g of needlets melting at 193°-194° C. (decompn.) TLC, silica gel Rf=0.28 (n-butanol-acetic acid-water=4:1:1)

Sources & evidence

ORD record
ord-b8214e2b637a4974b7ebd09f9db9345b
Source dataset
uspto-grants-1993_08
Patent number
US05232913

Reaction notes

Loading…