Citric Acid → HCID 178512808, compound

HRID 746164Notes

Reaction equation

HRID 746164 reaction equation
Cl.N(CCCCCCC(N)=O)C(N)=N.Cl.Cl.NCCCNCCCCNC(=O)C(O)O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.Cl.Cl.Cl.[NH2:48][CH2:49][CH2:50][CH2:51][NH:52][CH2:53][CH2:54][CH2:55][CH2:56][NH:57][C:58](=[O:74])[CH:59]([NH:61][C:62](=[O:73])[CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][NH:69][C:70]([NH2:72])=[NH:71])[OH:60]>O>[NH2:48][CH2:49][CH2:50][CH2:51][NH:52][CH2:53][CH2:54][CH2:55][CH2:56][NH:57][C:58](=[O:74])[CH:59]([NH:61][C:62](=[O:73])[CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][NH:69][C:70]([NH2:72])=[NH:71])[OH:60]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 133564GlyoxylylspermidineHCID 178478610HCID 178478610, compoundHCID 178479429HCID 178479429, compound

Product 1

HCID 178512808HCID 178512808, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

A mixture of 18 g (80.9 mmoles) of 7-guanidinoheptanamide hydrochloride, 23.6 g (80.9 moles) of N-[4-(3-aminopropyl)aminobutyl]-2,2-dihydroxyethanamide dihydrochloride obtained in Example 4, and 5.7 g (27 mmoles) of citric acid in water (200 ml) was evaporated to dryness to give a syrup which contained 1.6 g of water. The resulting syrup was heated at 60° C. for 8 hours and purifiled in a procedure similar to that in Example 5 giving 19.0 g (47.3% yield) of white powder of N-[4-(3-aminopropyl)aminobutyl]-2-(7-guanidinoheptanamido)-2-hydroxyethanamide trihydrochloride.

Workup

  1. customwas evaporated to dryness
  2. customto give a syrup which

Sources & evidence

ORD record
ord-e5ba9395c0294a868127282bfae7de17
Source dataset
uspto-grants-1986_07
Patent number
US04603015

Reaction notes

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