Pyridine water → HCID 87592395, compound

HRID 2100227Notes

Reaction equation

HRID 2100227 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

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. temperatureThe resulting solution was heated at 53 C
  3. concentrationThe solution was then concentrated
  4. customto give a white solid residue
  5. filtrationThe crude product was purified by gel filtration (Sephadex LH20; water)
  6. customto give BHAlyslys2lys4lys8lys16lys32 with 64 sodium 3,6-disulfophenylurea groups as a white fluffy solid

Sources & evidence

ORD record
ord-b4172f7987914fa8ba84c79b4d6f981f
Source dataset
uspto-grants-2009_08
Patent number
US07572459B2

Reaction notes

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