Dicyclohexylcarbodiimide → Fmoc-asn(trt)-opfp

HRID 1110196

Reaktionsgleichung

Reaktionsgleichung von HRID 1110196
[NH:1]([C:29]([O:31][CH2:32][CH:33]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[C:39]2[C:34]1=[CH:35][CH:36]=[CH:37][CH:38]=2)=[O:30])[C@H:2]([C:26]([OH:28])=[O:27])[CH2:3][C:4](=[O:25])[NH:5][C:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[F:46][C:47]1[C:52](O)=[C:51]([F:54])[C:50]([F:55])=[C:49]([F:56])[C:48]=1[F:57].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[NH:1]([C:29]([O:31][CH2:32][CH:33]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[C:39]2[C:34]1=[CH:35][CH:36]=[CH:37][CH:38]=2)=[O:30])[C@H:2]([C:26]([O:28][C:52]1[C:47]([F:46])=[C:48]([F:57])[C:49]([F:56])=[C:50]([F:55])[C:51]=1[F:54])=[O:27])[CH2:3][C:4](=[O:25])[NH:5][C:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Komponenten

5

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 13041PentafluorophenolHCID 640248Fmoc-Asn(Trt)-OH

Produkt 1

HCID 15138257Fmoc-asn(trt)-opfp

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1.5 g (2.51 mmol) of Fmoc-Asn(Trt)-OH are dissolved in 15 ml of tetrahydrofuran. 0.51 g (2.76 mmol) of pentafluoro-phenol is added, the solution is cooled to 0° and then 0.57 g (2.76 mmol) of dicyclohexyl-carbodiimide is also added in solid form. It is stirred at 0° for 30 minutes, at room temperature for 2 hours and again at 0° for 30 minutes. The dicyclohexylurea which has crystallized out is filtered off, and the filtrate is evaporated to dryness and triturated with 40 ml of diisopropyl ether. The powdery residue is filtered off, dried and recrystallized from methylene chloride/petroleum ether. Fmoc-Asn(Trt)-OPfp is obtained; m.p. 154°-156°, [α]D20 =-7.8° (THF).

Aufarbeitung

  1. temperaturethe solution is cooled to 0°
  2. customThe dicyclohexylurea which has crystallized out
  3. filtrationis filtered off
  4. customthe filtrate is evaporated to dryness
  5. customtriturated with 40 ml of diisopropyl ether
  6. filtrationThe powdery residue is filtered off
  7. customdried
  8. customrecrystallized from methylene chloride/petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-81158b16d707489b8214ac7ac824e4a5
Quelldatensatz
uspto-grants-1994_06
Patentnummer
US05324833

Verknüpfte Notizen

Wird geladen…