Acetyl chloride → 3054-47-5

HRID 1769816Notes

Reaction equation

HRID 1769816 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].C(Cl)(=O)C(C)(C)C.[CH2:12]([C@H:27]([NH2:31])[C:28]([OH:30])=[O:29])[CH2:13][C:14]([NH:16][C@H:17]([C:20]([NH:22][CH2:23][C:24]([OH:26])=[O:25])=[O:21])[CH2:18][SH:19])=[O:15]>CC(C)=O.O.CC(C)=O>[NH2:31][C@H:27]([C:28]([OH:30])=[O:29])[CH2:12][CH2:13][C:14]([NH:16][C@H:17]([C:20]([NH:22][CH2:23][C:24]([OH:26])=[O:25])=[O:21])[CH2:18][S:19][C:1](=[O:3])[CH3:2])=[O:15]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 62493Pivaloyl chlorideHCID 124886Glutathione

Product 1

HCID 98943723054-47-5Yield 85%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

Using in the procedure of Example 1 acetyl chloride, in place of pivaloyl chloride, L-glutathione reduced (15.4 g) provides, after usual work-up, a crude white solid which is dissolved in warm acetone/water (2/1; 40° C.; 300 ml). The obtained solution is further diluted with more acetone (100 ml) and cooled on ice-water bath. After about two hours the white crystalline precipitate is collected, washed with the solvent (40 ml) and dried under vacuum affording γ-L-glutamyl-S-acetyl-L-cysteinyl-glycine (14.8 g yield=85%)

Workup

  1. customprovides
  2. temperaturecooled on ice-water bath
  3. customAfter about two hours the white crystalline precipitate is collected
  4. washwashed with the solvent (40 ml)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-d42a66c30acc43119a0bad79addf5c0c
Source dataset
uspto-grants-1995_01
Patent number
US05382679

Reaction notes

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