Reaktion #94670

ord-2019574de9bf4a3f9f66054b1f3086e5

Reaktionsgleichung

NC(=O)C1=CN([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)C=CC1
NAD
O=C1NC(=O)c2ccccc21
phthalimide
Cl
hydrochloric acid
→
Cl.Cl.NCCCc1cn[nH]c1
4-(3-aminopropyl)-pyrazole dihydrochloride

Edukte

NC(=O)C1=CN([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)C=CC1
NAD
O=C1NC(=O)c2ccccc21
phthalimide
Cl
hydrochloric acid
—
alcohol

Reagenzien

Keine

Reaktionsbedingungen

Temperatur
4°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigephthalic acid removed by filtration
  2. 2
    Sonstigethe filtrate evaporated to dryness
  3. 3
    Sonstigeto give a product which
  4. 4
    Sonstigeafter recrystallization
  5. 5
    workup.ADDITIONfrom a mixture of ethanol and ethyl ether
  6. 6
    SonstigeThis pyrazole compound could be coupled to the activated dextran by reaction of the terminal amino group

Vorschrift

This phthalimide intermediate (8.0 gram, 0.03 mole) was refluxed in 100 ml. of 6 normal hydrochloric acid overnight. The clear solution was cooled to 4° C., phthalic acid removed by filtration, and the filtrate evaporated to dryness to give a product which, after recrystallization from a mixture of ethanol and ethyl ether, amounted to 4.4 grams of a white solid identified as 4-(3-aminopropyl)-pyrazole dihydrochloride, melting point 189°-190° C. This pyrazole compound could be coupled to the activated dextran by reaction of the terminal amino group, but the resulting affinity resin, in which the coupling arm had a length of only 6 Angstrom units, had poor binding capacity for the binary complex of alcohol dehydrogenase and NAD.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04131727uspto-grants-1978_12