Triethylamine → N-(3'-Diethylaminopropyl)-aspartic acid-4-methyl ester

HRID 2286017

Reaction equation

HRID 2286017 reaction equation
[CH3:1][O:2][C:3](=[O:9])/[CH:4]=[CH:5]\[C:6]([OH:8])=[O:7].C(N(CC)CC)C.[CH2:17]([N:19]([CH2:24][CH3:25])[CH2:20][CH2:21][CH2:22][NH2:23])[CH3:18]>CCOCC>[CH3:1][O:2][C:3](=[O:9])[CH2:4][C@@H:5]([C:6]([OH:8])=[O:7])[NH:23][CH2:22][CH2:21][CH2:20][N:19]([CH2:24][CH3:25])[CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61011N,N-Diethyl-1,3-propanediamineHCID 5354456Monomethyl maleate

Product 1

HCID 54143349N-(3'-Diethylaminopropyl)-aspartic acid-4-methyl esterYield 53.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

71.5 g (0.5 mol+10% excess) of maleic acid-monomethyl ester are reacted, in the manner described in Example 1, with 100 ml of triethylamine and 65.1 g (0.5 mol) of 3-diethylaminopropylamine. The reaction product is mixed with 500 ml of ether, the mixture is filtered and the residue is washed with ether. After drying at 60° C. in vacuo, the crude product is recrystallised in acetone to yield 69.44 g (53.4% of theory) of a white crystalline aspartic acid derivative, the melting point of which is 154.5°-156.5° C.

Workup

  1. filtrationthe mixture is filtered
  2. washthe residue is washed with ether
  3. customAfter drying at 60° C. in vacuo
  4. customthe crude product is recrystallised in acetone

Sources & evidence

ORD record
ord-e0b64d7aba534dfbb0c7171d2a8ede1b
Source dataset
uspto-grants-1982_04
Patent number
US04326069

Linked notes

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