N-Acetyl-L-Cysteine → Bis-(2-Acetylamino-2-Carboxyethylthio)succinimidyl Hexane

HRID 1836167Notes

Reaction equation

HRID 1836167 reaction equation
C1(=O)N([CH:6]([N:12]2[C:16](=[O:17])[CH:15]=[CH:14][C:13]2=[O:18])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])C(=O)C=C1.[C:21]([NH:24][C@H:25]([C:28]([OH:30])=[O:29])[CH2:26][SH:27])(=[O:23])[CH3:22]>N1C=CC=CC=1>[C:21]([NH:24][CH:25]([C:28]([OH:30])=[O:29])[CH2:26][S:27][C:6]([S:27][CH2:26][CH:25]([C:28]([OH:30])=[O:29])[NH:24][C:21](=[O:23])[CH3:22])([N:12]1[C:13](=[O:18])[CH2:14][CH2:15][C:16]1=[O:17])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])(=[O:23])[CH3:22]

Participants

4

Reactant 2

HCID 12035N-Acetyl-L-CysteineHCID 18179261Bismaleimidohexane

Product 1

HCID 86759503Bis-(2-Acetylamino-2-Carboxyethylthio)succinimidyl Hexane

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
40 °C

Procedure

Bis-maleimidohexane (0.05 g, 1.81×10−4 mol) and N-acetylcysteine (0.059 g, 3.62×10−4 mol) were dissolved in pyridine (1 ml). The reaction was stirred at 40° C. for 24 h. The solvent was removed in vacuo and the residue was dissolved in ethanol (5 ml) and the solvent removed in vacuo. This procedure was repeated 3 times more. The residue of the title compound weighed 0.1 g.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in ethanol (5 ml)
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-06f1138f7d554dd480ee86b535a46701
Source dataset
uspto-grants-2004_08
Patent number
US06777190B1

Reaction notes

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