L-Aspartic Acid → N-(3'-Cyclohexylaminopropyl)-aspartic acid-4-ethyl ester

HRID 894730

Reaction equation

HRID 894730 reaction equation
[CH2:1]([O:3][C:4](=[O:10])/[CH:5]=[CH:6]\[C:7]([OH:9])=[O:8])[CH3:2].[CH:11]1([NH:17][CH2:18][CH2:19][CH2:20][NH2:21])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.N[C@H](C(O)=O)CC(O)=O>C(N(CC)CC)C>[CH2:1]([O:3][C:4](=[O:10])[CH2:5][C@@H:6]([C:7]([OH:9])=[O:8])[NH:21][CH2:20][CH2:19][CH2:18][NH:17][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[CH3:2]

Participants

5

Reactant 3

HCID 5960L-Aspartic AcidHCID 18718N-Cyclohexyl-1,3-propanediamineHCID 5354457Monoethyl maleate

Product 1

HCID 22817116N-(3'-Cyclohexylaminopropyl)-aspartic acid-4-ethyl ester

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In a manner analogous to that of Example 1, 394.3 g (2.4 mols+14% excess) of maleic acid-monoethyl ester are placed into the glass flask, and 480 ml of triethylamine are added dropwise with cooling. There are subsequently added 372.6 g (2.4 mols) of 3-cyclohexylaminopropylamine, and the reaction mixture is reacted for 25 minutes at 84°-86° C. It is further processed according to Example 1 and the yield is 546.8 g (75.7% of theory) of a white crystalline aspartic acid derivative, which decomposes at 152° C.

Workup

  1. additionare added dropwise
  2. temperaturewith cooling
  3. customthe reaction mixture is reacted for 25 minutes at 84°-86° C
  4. customdecomposes at 152° C.

Sources & evidence

ORD record
ord-5450adb32c4c4184bf150a0dcbe8579f
Source dataset
uspto-grants-1981_08
Patent number
US04284755

Linked notes

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