N-(1,1-Dimethylethyl)-1,3-propanediamine → N-(3'-tert-Butylaminopropyl)-aspartic acid-4-ethyl ester

HRID 894733

Reaction equation

HRID 894733 reaction equation
[CH2:1]([O:3][C:4](=[O:10])/[CH:5]=[CH:6]\[C:7]([OH:9])=[O:8])[CH3:2].[C:11]([NH:15][CH2:16][CH2:17][CH2:18][NH2:19])([CH3:14])([CH3:13])[CH3:12]>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:19][CH2:18][CH2:17][CH2:16][NH:15][C:11]([CH3:14])([CH3:13])[CH3:12])[CH3:2]

Participants

4

Reactant 2

HCID 40274N-(1,1-Dimethylethyl)-1,3-propanediamineHCID 5354457Monoethyl maleate

Product 1

HCID 22817119N-(3'-tert-Butylaminopropyl)-aspartic acid-4-ethyl esterYield 77.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In a manner analogous to that of Example 1, 400 ml of triethylamine are added to 317 g (2.2 mols) of maleic acidmonoethyl ester, and the mixture is subsequently reacted with 260 g (2.0 mols) of 3-tert-butylaminopropylamine. The reaction mixture is further processed as in Example 1 to yield 423.4 g (77.2% of theory) of a white crystalline aspartic acid derivative, which melts at 174°-175° C. after recrystallisation in a mixture of ethanol/acetone (1:3).

Sources & evidence

ORD record
ord-bab73897971d413aa15e6d28c1b00fdb
Source dataset
uspto-grants-1981_08
Patent number
US04284755

Linked notes

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