Sodium Carbonate → HCID 86756422, compound

HRID 2100224Notes

Reaction equation

HRID 2100224 reaction equation
[S:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:15])[CH:13]=[CH2:14])=[CH:7][CH:6]=1)([OH:4])(=[O:3])=[O:2].[Na:16].C(=O)([O-])[O-].[Na+].[Na+]>O>[S:1]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12](=[O:15])[CH2:13][CH3:14])=[CH:9][CH:10]=1)([OH:4])(=[O:3])=[O:2].[Na:16]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 86756423HCID 86756423, compound

Product 1

HCID 86756422HCID 86756422, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Solid sodium N-(4-sulfophenyl)acrylamide (250 mg; 1 mmol) and solid sodium carbonate (106 mg; 1 mmol) were added successively to a stirred solution of PAMAM 4.0 (EDA) (78 mg; 0.011 mmol) in water (4 ml). The resulting solution was stirred under nitrogen for four days and then freeze dried to give a fluffy white solid. The crude product was purified by gel filtration (Sephadex LH20; water to give PAMAM 4.0 (EDA) terminated with 64 sodium N-(4-sulfophenyl)propanamide groups (206 mg). 13C nmr showed a faint trace of what was taken to be mono alkylated terminal amino groups. 1H nmr (D2O): δ2.10; 2.48; 2.58; 2.79; 3.20; 7.42 (d, J=7 Hz); 7.65 (d, J=7 Hz). 13C nmr (D2O): δ36.5; 37.9; 41.1; 53.4; 55.6; 124.8; 130.9; 143.0; 144.2; 177.4; 178.5.

Workup

  1. customfreeze dried
  2. customto give a fluffy white solid
  3. filtrationThe crude product was purified by gel filtration (Sephadex LH20
  4. customwater to give PAMAM 4.0 (EDA)
  5. customterminated with 64 sodium N-(4-sulfophenyl)propanamide groups (206 mg)

Sources & evidence

ORD record
ord-bb3d44d6d700475890f1446c0f91a48f
Source dataset
uspto-grants-2009_08
Patent number
US07572459B2

Reaction notes

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