Sodium Bicarbonate → HCID 12794729, compound

HRID 2100226Notes

Reaction equation

HRID 2100226 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-9788a6b4d9894600a203f2f2c69240ed
Source dataset
uspto-grants-2009_08
Patent number
US07572459B2

Reaction notes

Loading…