Sodium Bicarbonate → HCID 12794729, compound

HRID 2230755Notes

Reaction equation

HRID 2230755 reaction equation
[C:1]([BH3-])#[N:2].[Na+].C([C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[C:9]([OH:16])[CH:8]=1)=O.C(=O)([O-])O.[Na+]>O>[C:11]([C:10]1[CH:14]=[CH:15][C:7]([CH2:1][NH2:2])=[CH:8][C:9]=1[OH:16])([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 6568764-Formyl-2-hydroxybenzoic acidHCID 5003444Sodium cyanoborohydride

Product 1

HCID 12794729HCID 12794729, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium cyanoborohydride (32 mg; 0.5 mmol) was added to a mixture of PAMAM 4.0 (EDA) (69 mg; 0.01 mmol), 4-formyl-2-hydroxybenzoic acid (83 mg; 0.5 mmol), and sodium hydrogen carbonate (42 mg; 0.5 mmol) in water (4 ml). The inhomogeneous orange mixture was stirred for four hours at room temperature, during which time it became homogeneous. The orange solution was then concentrated and the residue purified by gel filtration (Sephadex LH20; water) to give PAMAM 4.0 (EDA) terminated with ca. 32 4-carboxy-3-hydroxybenzylamine groups (91 mg). 1H and 13C nmr (D2O) shows mostly mono alkylation but with some signs of dialkylation of the terminal amino groups, both spectra show broad peaks. 13C nmr (D2O): δ37.0; 41.1; 50.9; 53.4; 55.5; 55.8; 61.5; 120.9; 122.2; 122.4; 132.3; 132.7; 135.0; 135.8; 163.5; 163.7; 169.0; 178.6; 179.3. 1H nmr (D2O): δ2.20; 2.35; 2.60; 3.15; 3.30; 3.55; 4.25; 6.68; 7.12; 7.55.

Workup

  1. concentrationThe orange solution was then concentrated
  2. filtrationthe residue purified by gel filtration (Sephadex LH20; water)
  3. customto give PAMAM 4.0 (EDA)
  4. customterminated with ca. 32 4-carboxy-3-hydroxybenzylamine groups (91 mg)

Sources & evidence

ORD record
ord-7641d25f3cd748868f97d6fdd9725128
Source dataset
uspto-grants-2002_07
Patent number
US06426067B1

Reaction notes

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