Ethyl isocyanatoacetate → Dihexyl aspartate carbamate

HRID 518910

Reaction equation

HRID 518910 reaction equation
N(C[C:5]([O:7]CC)=[O:6])=C=O.[N:10]([CH:13]([CH2:23][C:24]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:25])[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:15])=C=O>CN(C=O)C.CS(C)=O.O>[C:5](=[O:6])([OH:7])[NH2:10].[NH2:10][C@H:13]([C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:15])[CH2:23][C:24]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:25]

Participants

5

Reactant 2

HCID 76283Ethyl isocyanatoacetateHCID 86656430HCID 86656430, compound

Product 1

HCID 86656429Dihexyl aspartate carbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3013483N,N-dimethylformamide; methylsulfinylmethaneSolvent

Procedure

2.7 g (i.e., 50 mmol of hydroxyls) of dextran with a weight-average molar mass of approximately 10 kg/mol (Bachem) are dissolved in a DMF/DMSO mixture. The mixture is brought to 130° C. with stirring and 3.2 g (25 mmol) of ethyl isocyanatoacetate and then 3.9 g (8 mmol) of dihexyl 2-isocyanatobutanedioate are gradually introduced. After reacting for 1 h, the medium is diluted in water and purified by diafiltration through a 5 kD PES membrane against 0.1N NaOH, 0.9% NaCl and water. The final solution is quantitatively determined by dry extract, in order to determine the concentration of polymer. A fraction of solution is lyophilized and analyzed by 1H NMR in D2O in order to determine the degree of conversion of the hydroxyls to N-(sodium methylcarboxylate) carbamate and the degree of the functionalization of the hydroxyls to give dihexyl aspartate carbamate.

Workup

  1. customis brought to 130° C.
  2. filtrationpurified by diafiltration through a 5 kD PES membrane against 0.1N NaOH, 0.9% NaCl and water
  3. customby dry
  4. extractionextract, in order

Sources & evidence

ORD record
ord-17fc1b3fe5f0430aa9b1b5535a8d6449
Source dataset
uspto-grants-2015_08
Patent number
US09115218B2

Linked notes

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