N,N-Dimethylethylenediamine → Asparaginamide

HRID 861204

Reaction equation

HRID 861204 reaction equation
C[N:2]([CH2:4][CH2:5][NH2:6])C.[OH:7][C:8]1[CH:13]=CC=C[N:9]=1.NC([OH:17])C>CN(C=O)C>[NH2:2][C@H:4]([C:5]([NH2:6])=[O:17])[CH2:13][C:8]([NH2:9])=[O:7]

Participants

5

Reactant 3

HCID 66053N,N-DimethylethylenediamineHCID 522583Acetaldehyde ammoniaHCID 178516071HCID 178516071, compound

Product 1

HCID 447212Asparaginamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

15 g (155 mmol) of polyanhydroaspartic acid (Mvisc. =19,000) are dissolved in 80 ml of DMF (anhydrous), if appropriate with gentle warming. First, 3.40 g (39 mmol) of freshly distilled dimethylaminoethylamine diluted in 20 ml of DMF are added dropwise to this solution and 1 g of anhydrous 2-hydroxypyridine is added and the mixture is stirred at room temperature for one day. 10 g (164 mmol) of aminoethanol are then added. After stirring for a further day the mixture is warmed at 50° C. for 2 h and repeatedly precipitated in anhydrous acetone.

Workup

  1. additionis added
  2. stirringAfter stirring for a further day the mixture
  3. temperatureis warmed at 50° C. for 2 h
  4. customrepeatedly precipitated in anhydrous acetone

Sources & evidence

ORD record
ord-0c3cb4879afb47d09978f2b4aa93cba1
Source dataset
uspto-grants-1998_02
Patent number
US05714138

Linked notes

Loading…