Dicyclohexylcarbodiimide → 6-[5-(1-Pyrenecarbonylamino)-1-pentanyl]-3,10-bis(2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo[10.3.1]-hexadeca-1(16),12,14-triene

HRID 636321

Reaktionsgleichung

Reaktionsgleichung von HRID 636321
[C:1]1([C:17](O)=[O:18])[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.[NH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][N:51]1[CH2:65][CH2:64][CH2:63][N:62]([S:66]([C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][C:70]=2[N+:75]([O-:77])=[O:76])(=[O:68])=[O:67])[CH2:61][C:60]2[N:78]=[C:56]([CH:57]=[CH:58][CH:59]=2)[CH2:55][N:54]([S:79]([C:82]2[CH:87]=[CH:86][CH:85]=[CH:84][C:83]=2[N+:88]([O-:90])=[O:89])(=[O:81])=[O:80])[CH2:53][CH2:52]1>C1COCC1>[C:1]1([C:17]([NH:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][N:51]2[CH2:65][CH2:64][CH2:63][N:62]([S:66]([C:69]3[CH:74]=[CH:73][CH:72]=[CH:71][C:70]=3[N+:75]([O-:77])=[O:76])(=[O:67])=[O:68])[CH2:61][C:60]3[N:78]=[C:56]([CH:57]=[CH:58][CH:59]=3)[CH2:55][N:54]([S:79]([C:82]3[CH:87]=[CH:86][CH:85]=[CH:84][C:83]=3[N+:88]([O-:90])=[O:89])(=[O:81])=[O:80])[CH2:53][CH2:52]2)=[O:18])[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 1253951-Pyrenecarboxylic acidHCID 105803766-(5-Amino-1-pentanyl)-3,10-bis(2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo[10.3.1]hexadeca-1(16),12,14-triene

Produkt 1

HCID 105576846-[5-(1-Pyrenecarbonylamino)-1-pentanyl]-3,10-bis(2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo[10.3.1]-hexadeca-1(16),12,14-trieneAusbeute 65,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 1-pyrenecarboxylic acid (0.22 g, 0.89 mmol) and 4-methymoroholine (0.12 g, 1.14 mmol) in 5 mL of anhydrous THF was stirred for 30 min. After addition of DCC (0.16 g, 0.76 mmol) and HOBT (0.11 g, 0.76 mmol), the solution was stirred another 30 min. A solution of 6-(5-amino-1-pentanyl)-3,10-bis(2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo[10.3.1]hexadeca-1(16),12,14-triene (0.51 g, 0.76 mmol) was added into the above solution and stirred at rt overnight. The solvent was evaporated and the residue was dissolved in CH2Cl2. The resulting solution was washed with 5% NaHCO3 solution and brine, dried and concentrated. The residue was purified by flash chromatography on a silica gel column using 100:1 CH2Cl2—MeOH as an eluent to give 0.45 g (65%) of the title compound as a yellow foam.

Aufarbeitung

  1. stirringstirred at rt overnight
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in CH2Cl2
  4. washThe resulting solution was washed with 5% NaHCO3 solution and brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-a597bda3d8354311a8f782086389df2c
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06191273B1

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