Pyridine → Darinaparsin

HRID 751477

Reaction equation

HRID 751477 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].[CH3:21][As:22]([CH3:24])Cl.N1C=CC=CC=1>COCCOC>[CH3:21][As:22]([CH3:24])[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]

Participants

5

Reactant 3

HCID 1049PyridineHCID 11200ChlorodimethylarsineHCID 124886Glutathione

Product 1

HCID 11683005Darinaparsin

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

In a 500 mL flask, 7 g of glutathione was used as received from the Aldrich Chemical Co., purity 98% and dissolved in 250 mL of 1,2-dimethoxyethane. To this solution was added 3.3 g of dimethylchloroarsine. This was followed by the addition of 3.5 g of pyridine (redistilled after drying over NaOH pellets). The solution was refluxed for one hour after which time it was stirred at room temperature for three hours.

Workup

  1. temperatureThe solution was refluxed for one hour after which time it

Sources & evidence

ORD record
ord-1d2d7a40ffad4f6f89dc233d9c543997
Source dataset
uspto-grants-2008_07
Patent number
US07405314B2

Linked notes

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