Hydrogen Peroxide → HCID 88295758, compound

HRID 1420120Notes

Reaction equation

HRID 1420120 reaction equation
[C:1]([NH:4][C@H:5]([C:8]([OH:10])=[O:9])[CH2:6][SH:7])(=[O:3])[CH3:2].[C:11]([NH:16][C@H:17]([C:20]([OH:22])=[O:21])[CH2:18][SH:19])(=[O:15])[CH:12]([CH3:14])[CH3:13].OO>CO>[C:1]([NH:4][C@@H:5]([CH2:6][S:7][S:19][CH2:18][C@H:17]([NH:16][C:11](=[O:15])[CH:12]([CH3:13])[CH3:14])[C:20]([OH:22])=[O:21])[C:8]([OH:10])=[O:9])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 12035N-Acetyl-L-CysteineHCID 130211N-Isobutyrylcysteine

Product 1

HCID 88295758HCID 88295758, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-acetyl-L-cysteine (0.652 g, 4 mmol) and N-isobutyryl-L-cysteine (0.764 g, 4 mmol) in 10 mL of MeOH was stirred while hydrogen peroxide (30%, 0.60 mL, 5 mmol) was added dropwise. The stirring was continued for 3 hours at room temperature, after which the solvent was removed on the rotary evaporator. Addition of 25 mL of acetone and repeated evaporation afforded 1.5 g of crude material as an oil which solidified on standing. The desired title compound was isolated from this mixture by preparative HPLC as described in Example 17.

Workup

  1. additionwas added dropwise
  2. customafter which the solvent was removed on the rotary evaporator
  3. additionAddition of 25 mL of acetone
  4. customevaporation
  5. customafforded 1.5 g of crude material as an oil which

Sources & evidence

ORD record
ord-967f72ec8ba8490a9f9bd4251155b0f6
Source dataset
uspto-grants-1999_03
Patent number
US05889050

Reaction notes

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