Cacodyl → Darinaparsin

HRID 751478Notes

Reaction equation

HRID 751478 reaction equation
C[As]([NH:4][C@@H:5]([CH2:9][CH2:10][C:11]([NH:13][C@H:14]([C:17]([NH:19][CH2:20][C:21]([OH:23])=[O:22])=[O:18])[CH2:15][SH:16])=[O:12])[C:6]([OH:8])=[O:7])C.[CH3:24][As:25](N(SSN([As](C)C)[C@H](C(O)=O)CCC(=O)N)[C@H](C(O)=O)CCC(=O)N)[CH3:26].C[As]([As](C)C)C>ClCCl>[CH3:24][As:25]([CH3:26])[S:16][CH2:15][C@@H:14]([C:17]([NH:19][CH2:20][C:21]([OH:23])=[O:22])=[O:18])[NH:13][C:11](=[O:12])[CH2:10][CH2:9][C@@H:5]([C:6]([OH:8])=[O:7])[NH2:4]

Participants

5

Reactant 3

HCID 79018CacodylHCID 86605429DimethylarsinoglutathioneHCID 86605430Dithiobis(dimethylarsinoglutamine)

Product 1

HCID 11683005Darinaparsin

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dimethylarsinoglutathione is made using an adapted of Chen (Chen, G. C., et al. Carbohydrate Res. (1976) 50: 53-62) the contents of which are hereby incorporated by reference in their entirety. Briefly, dithiobis(dimethylarsinoglutamine) is dissolved in dichloromethane under nitrogen. Tetramethyldiarsine is added dropwise to the solution and the reaction is stirred overnight at room temperature under nitrogen and then exposed to air for 1 h. The mixture is then evaporated to dryness and the residue is washed with water and dried to give a crude solid that is recrystallized from methanol to give S-dimethylarsinoglutathione.

Workup

  1. waitexposed to air for 1 h
  2. customThe mixture is then evaporated to dryness
  3. washthe residue is washed with water
  4. customdried
  5. customto give a crude solid that
  6. customis recrystallized from methanol

Sources & evidence

ORD record
ord-fbe5557114d54f7eb20102551c6c26cb
Source dataset
uspto-grants-2008_07
Patent number
US07405314B2

Reaction notes

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