Réaction #1256730

ord-5ea673af3dfc433898ef8a9a9355e419

Équation de réaction

O=S(=O)([O-])c1cc(O)c2ccc3c(S(=O)(=O)[O-])cc(S(=O)(=O)[O-])c4ccc1c2c34.[Na+].[Na+].[Na+]
HPTS
O=S(=O)(O)O
sulfuric acid
→
O=S(=O)([O-])c1cc2c(O)ccc3ccc4cccc1c4c32.[Na+]
sodium 3-hydroxypyrene-5-sulfonate
Rendement 10.0%

Réactifs

O=S(=O)([O-])c1cc(O)c2ccc3c(S(=O)(=O)[O-])cc(S(=O)(=O)[O-])c4ccc1c2c34.[Na+].[Na+].[Na+]
HPTS
O=S(=O)(O)O
sulfuric acid

Réactifs

Aucun

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreThe synthesis of mono-CysMA

Mode opératoire

The synthesis of mono-CysMA is given in Scheme 1. Reaction of HPTS with 30% sulfuric acid at 150° C. for 20 min gave sodium 3-hydroxypyrene-5-sulfonate 1 in 10% yield. Acetylation of 1 followed by chlorination of 2 gave intermediate 3, which is analogous to HPTS-Cl but with only one sulfonyl chloride. The polymerizable group was attached via the cysteic acid moiety and reacted with 3 to give compound 4. Chlorosulfonation of 4 was achieved without affecting the polymerizable group and after purification on polystyrene beads gave mono-CysMA in 50% yield over two steps. The dye was characterized by 1H NMR, HPLC, and MS.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07824918B2uspto-grants-2010_11