Benzoyl chloride → HCID 18658589, compound

HRID 1769817Notes

Reaction equation

HRID 1769817 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10]([C@H:25]([NH2:29])[C:26]([OH:28])=[O:27])[CH2:11][C:12]([NH:14][C@H:15]([C:18]([NH:20][CH2:21][C:22]([OH:24])=[O:23])=[O:19])[CH2:16][SH:17])=[O:13]>CC(C)=O.O>[NH2:29][C@H:25]([C:26]([OH:28])=[O:27])[CH2:10][CH2:11][C:12]([NH:14][C@H:15]([C:18]([NH:20][CH2:21][C:22]([OH:24])=[O:23])=[O:19])[CH2:16][S:17][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:13]

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 124886Glutathione

Product 1

HCID 18658589HCID 18658589, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

Using in the procedure of Example 1 benzoyl chloride in place of pivaloyl chloride, L-glutathione reduced (15.4 g) affords a crude white solid which is suspended in boiling acetone/water (3/1; 400 ml) for thirty minutes. After cooling at room temperature the white precipitate is collected by filtration and washed with acetone (20 ml). Under vacuum drying yields γ-L-glutamyl-S-benzoyl-L-cysteinyl-glycine (16 g yield=78%).

Workup

  1. customaffords a crude white solid which
  2. customfor thirty minutes
  3. filtrationis collected by filtration
  4. washwashed with acetone (20 ml)
  5. customUnder vacuum drying

Sources & evidence

ORD record
ord-58d3122bc02d4702898032da4d68e2f1
Source dataset
uspto-grants-1995_01
Patent number
US05382679

Reaction notes

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