1,2-Dichloroethane → HCID 178525997, Verbindung

HRID 2174361Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2174361
C1C=CC(C(Cl)(C2C(Cl)=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C2C(COC([NH:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][O:45][CH2:46][C:47]([OH:49])=[O:48])=O)C3C(=CC=CC=3)C=2C=CC=1.CCN(C(C)C)C(C)C.[NH:59]1[C:63]([CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][C:79]([OH:81])=O)=[N:62][N:61]=[N:60]1.ON1C(=O)C2C=CC=CC=2N=N1.C(Cl)CCl>ClCCl.CO>[NH:62]1[C:63]([CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][C:79]([NH:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][O:45][CH2:46][C:47]([OH:49])=[O:48])=[O:81])=[N:59][N:60]=[N:61]1

Komponenten

9

Edukt 6

HCID 111,2-DichloroethaneHCID 730263-hydroxy-1,2,3-benzotriazin-4(3H)-oneHCID 81531DiisopropylethylamineHCID 945242-Chlorotrityl chlorideHCID 27560922-(2-(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)ethoxy)ethoxy)acetic acidHCID 178525417HCID 178525417, Verbindung

Produkt 1

HCID 178525997HCID 178525997, VerbindungAusbeute 38,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel4×

Versuchsvorschrift

To a suspension of 2-chlorotrityl chloride resin (2 g; crosslinked polystyrene) in dichloromethane were added a solution of (2-(2-(9H-fluoren-9-ylmethoxycarbonylamino)ethoxy)ethoxy)acetic acid (0.55 g, 1.43 mmol) in dichloromethane (15 ml) and then a solution of DIPEA (0.65 ml) in dichloromethane (7 ml). After stirring at room temperature for 20 min methanol (2 ml) was added, and stirring was continued for 10 min. The resin was filtered, washed twice with dichloromethane and once with DMF. The resin was treated with a 20%-solution of piperidine in DMF (2×10 min), and washed extensively with DMF and dichloromethane. A solution of 16-(5-tetrazolyl)hexadecanoic acid (1.0 g, 3.08 mmol), 3-hydroxy-3,4-dihydro-1,2,3-benzotriazin-4-one (0.49 g, 3.0 mmol), and EDC (0.58 g, 3.03 mmol) in dichloromethane (25 ml) was added to the resin, and the mixture was shaken for 60 h. The resin was then extensively washed with DMF, dichloromethane and methanol, and suspended in a mixture of trifluoroacetic acid and dichloromethane (25:75; vol). After 0.5 h the resin was filtered, rinsed with dichloromethane, the combined filtrates were concentrated and the residue recrystallized from MeCN to yield 0.26 g of the title compound.

Aufarbeitung

  1. additionwas added
  2. filtrationThe resin was filtered
  3. washwashed twice with dichloromethane and once with DMF
  4. additionThe resin was treated with a 20%-solution of piperidine in DMF (2×10 min)
  5. washwashed extensively with DMF and dichloromethane
  6. stirringthe mixture was shaken for 60 h
  7. washThe resin was then extensively washed with DMF, dichloromethane and methanol
  8. additionsuspended in a mixture of trifluoroacetic acid and dichloromethane (25:75; vol)
  9. filtrationAfter 0.5 h the resin was filtered
  10. washrinsed with dichloromethane
  11. concentrationthe combined filtrates were concentrated
  12. customthe residue recrystallized from MeCN

Quellen und Nachweise

ORD-Eintrag
ord-451d708f99e54933b37bce465f5c4ba9
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09061067B2

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