Triethylamine → Fmoc-Asn(Trt)-OH

HRID 1110189

Reaktionsgleichung

Reaktionsgleichung von HRID 1110189
C1C(=O)N([O:8][C:9]([O:11][CH2:12][CH:13]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]3[C:14]2=[CH:15][CH:16]=[CH:17][CH:18]=3)=O)C(=O)C1.C(N(CC)CC)C.[NH2:33][C@H:34]([C:58]([OH:60])=[O:59])[CH2:35][C:36](=[O:57])[NH:37][C:38]([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.S(=O)(=O)(O)[O-].[K+]>O1CCCC1.O.C(OCC)(=O)C>[NH:33]([C:9]([O:11][CH2:12][CH:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:20]2[C:25]1=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:8])[C@H:34]([C:58]([OH:60])=[O:59])[CH2:35][C:36](=[O:57])[NH:37][C:38]([C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1

Komponenten

8

Edukt 4

HCID 8471Triethylamine2×HCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 516920Potassium bisulfateHCID 7408309N-(Triphenylmethyl)-L-asparagine

Produkt 1

HCID 640248Fmoc-Asn(Trt)-OH

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3.4 g of 9-fluorenylmethyl N-succinimidyl carbonate (10 mmol) are added and, at the same time, 1.4 ml of triethylamine are added dropwise so that the pH is 8.3-8.7 to a vigorously stirred solution of 3.8 g of H-Asn(Trt)-OH.0.5 H2O (10 mmol) in 20 ml of tetrahydrofuran, 10 ml of water and 1.4 ml of triethylamine (10 mmol). After 20 minutes, the mixture is cooled in an ice bath and ethyl acetate and 25 ml of a one-molar aqueous potassium bisulfate solution are added. The organic phase is washed with water until free of sulfate, dried over sodium sulfate and concentrated under reduced pressure to about 50 g. The Fmoc-Asn(Trt)-OH can be crystallized by slow addition of diisopropyl ether, m.p. 210°-211° (with decomposition).

Aufarbeitung

  1. temperaturethe mixture is cooled in an ice bath
  2. washThe organic phase is washed with water until free of sulfate
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure to about 50 g
  5. customThe Fmoc-Asn(Trt)-OH can be crystallized by slow addition of diisopropyl ether, m.p. 210°-211° (with decomposition)

Quellen und Nachweise

ORD-Eintrag
ord-6029d284f51645518896ddc67f84ada4
Quelldatensatz
uspto-grants-1994_06
Patentnummer
US05324833

Verknüpfte Notizen

Wird geladen…