Glutaric Acid → HCID 178512808, compound

HRID 703386Notes

Reaction equation

HRID 703386 reaction equation
Cl.[NH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([NH2:14])=[O:13])[C:3]([NH2:5])=[NH:4].Cl.Cl.[NH2:17][CH2:18][CH2:19][CH2:20][NH:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:31])[CH:28](O)[OH:29].C(O)(=O)CCCC(O)=O.Cl.Cl.Cl.NCCCC(N)CCCNC(=O)C(NC(=O)CCCCCCNC(N)=N)O>O>[NH2:17][CH2:18][CH2:19][CH2:20][NH:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:31])[CH:28]([NH:14][C:12](=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][NH:2][C:3]([NH2:5])=[NH:4])[OH:29]

Participants

6

Reactant 4

HCID 743Glutaric AcidHCID 133564GlyoxylylspermidineHCID 178478609HCID 178478609, compoundHCID 178479429HCID 178479429, compound

Product 1

HCID 178512808HCID 178512808, compoundYield 50.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

A mixture of 360 mg (1.62 mmoles) of 7-guanidinoheptanamide hydrochloride, 568 mg (1.94 mmoles) of N-[4-(3-aminopropyl)aminobutyl]-2,2-dihydroxyethanamide dihydrochloride, 214 mg (1.62 mmoles) of glutaric acid and 0.36 ml of water was heated at 60° C. for 24 hours. After completion of the reaction, 5 ml of water was added to the reaction mixture and the resulting mixture was purified in a manner similar to that in Example 1, using CM-Sephadex® C-25 (Na-type) and Sephadex® LH-20 to obtain 317 mg (39% yield) of a white powder of N-[4-(3-aminopropyl)-aminobutyl]-2-(7-guanidinoheptanamido)-2-hydroxyethanamide trihydrochloride.

Workup

  1. additionwas added to the reaction mixture
  2. customthe resulting mixture was purified in a manner similar to that in Example 1

Sources & evidence

ORD record
ord-4723753f85184005af6f475f00c5d60b
Source dataset
uspto-grants-1991_01
Patent number
US04983328

Reaction notes

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