Pyridine water → HCID 87591349, compound

HRID 2230759Notes

Reaction equation

HRID 2230759 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([N:13]=[C:14]=[S:15])[CH:7]=[C:8]([C:10]([OH:12])=[O:11])[CH:9]=1)([OH:3])=[O:2].[Na:16].[N:17]1C=CC=CC=1.O>>[C:10]([C:8]1[CH:7]=[C:6]([NH:13][C:14]([NH2:17])=[S:15])[CH:5]=[C:4]([C:1]([OH:3])=[O:2])[CH:9]=1)([OH:12])=[O:11].[Na:16]

Participants

3

Reactant 2

HCID 66926435Pyridine waterHCID 87592091HCID 87592091, compound

Product 1

HCID 87591349HCID 87591349, 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 (186 mg). The oil was dissolved in a 1:1 mixture of pyridine/water (8 ml) and sodium 3,5-dicarboxyphenyl isothiocyanate (450 mg; 2 mmol) added. The resulting solution was heated at 53° C. for 13 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-dicarboxyphenylurea 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-dicarboxyphenylurea groups as a white fluffy solid

Sources & evidence

ORD record
ord-d83abb8816c042c4b4b97f243f4fda96
Source dataset
uspto-grants-2002_07
Patent number
US06426067B1

Reaction notes

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