Réaction #470377

ord-9c57dc03620d4654bfc3504b55ad2625

Équation de réaction

C1CNCCNCCNCCN1
cyclen
O=C(OCc1ccccc1)C(Br)CCCN1C(=O)c2ccccc2C1=O
2-bromo-5-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pentanoic acid benzyl ester
O=C(OCc1ccccc1)C(CCCN1C(=O)c2ccccc2C1=O)N1CCNCCNCCNCC1
product
Rendement 81.3%
O=C(OCc1ccccc1)C(CCCN1C(=O)c2ccccc2C1=O)N1CCNCCNCCNCC1
5-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-2-(1,4,7,10-tetraazacyclododec-1-yl)pentanoic acid benzyl ester
Rendement 81.3%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    workup.ADDITIONare added dropwise
  2. 2
    FiltrationThe precipitate is filtered off
  3. 3
    Lavagewashed thoroughly with acetonitrile

Mode opératoire

55 g of cyclen base (320 mmol) are dissolved in 550 ml of CH3CN, to which 119.8 g of brominated derivative (2-bromo-5-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pentanoic acid benzyl ester, 288 mmol) dissolved in 550 ml of CH3CN are added dropwise. The medium is stirred at ambient temperature overnight. The precipitate is filtered off and washed thoroughly with acetonitrile. 138 g of product are obtained in the form of a white powder (corrected yield 81.3%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08367039B2uspto-grants-2013_02