Pyridine water → HCID 87592395, compound

HRID 991386Notes

Reaction equation

HRID 991386 reaction equation
[S:1]([C:5]1[CH:6]=[C:7]([N:15]=[C:16]=[S:17])[CH:8]=[C:9]([S:11]([OH:14])(=[O:13])=[O:12])[CH:10]=1)([OH:4])(=[O:3])=[O:2].[Na:18].[N:19]1C=CC=CC=1.O>>[S:1]([C:5]1[CH:6]=[C:7]([NH:15][C:16]([NH2:19])=[S:17])[CH:8]=[C:9]([S:11]([OH:14])(=[O:12])=[O:13])[CH:10]=1)([OH:4])(=[O:3])=[O:2].[Na:18]

Participants

3

Reactant 2

HCID 66926435Pyridine waterHCID 87591186HCID 87591186, compound

Product 1

HCID 87592395HCID 87592395, compound

Conditions

Temperature
53 °C

Procedure

Trifluoroacetic acid (3 ml) was added to a stirred suspension of BHAlyslys2lys4lys8lys16DBL32 (300 mg; 0.02 mmol) in dry dichloromethane (3 ml) and the resulting solution stirred at room temperature under nitrogen for two hours and then concentrated. The residue was dissolved in water and the solution passed through a column of Amberlite IRA 401 (OH) and the filtrate concentrated to give a viscous oil (187 mg). The oil was dissolved in a 1:1 mixture of pyridine/water (8 ml) and solid sodium 3,5-disulfophenyl isothiocyanate (680 mg; 2 mmol) added. The resulting solution was heated at 53° C. for three hours under nitrogen. The solution was then concentrated to give a white solid residue. The crude product was purified by gel filtration (Sephadex LH20; water) to give BHAlyslys2lys4lys8lys16lys32 with 64 sodium 3,6-disulfophenylurea groups as a white fluffy solid.

Workup

  1. additionadded
  2. concentrationThe solution was then concentrated
  3. customto give a white solid residue
  4. filtrationThe crude product was purified by gel filtration (Sephadex LH20; water)
  5. customto give BHAlyslys2lys4lys8lys16lys32 with 64 sodium 3,6-disulfophenylurea groups as a white fluffy solid

Sources & evidence

ORD record
ord-07f70e4971d14d6da0cd5d3086aaf06d
Source dataset
uspto-grants-2002_10
Patent number
US06464971B1

Reaction notes

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