p-Toluenesulfonic acid → Z-Gln-Trp-OBzl

HRID 1106301

Reaktionsgleichung

Reaktionsgleichung von HRID 1106301
[NH2:1][C@H:2]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.CC1C=CC(S(O)(=O)=O)=CC=1.[NH:34]([C:44]([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45])[C@H:35]([C:41](O)=[O:42])[CH2:36][CH2:37][C:38](=[O:40])[NH2:39].C1C2C3C(=O)N(O)C(=O)C3C1C=C2.C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1>[NH:34]([C:44]([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45])[C@H:35]([C:41]([NH:1][C@H:2]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)=[O:42])[CH2:36][CH2:37][C:38](=[O:40])[NH2:39]

Komponenten

7

Edukt 5

HCID 6101p-Toluenesulfonic acidHCID 10868DicyclohexylcarbodiimideHCID 75855L-Glutamine, N2-[(phenylmethoxy)carbonyl]-HCID 895293a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dioneHCID 7016092L-Tryptophan benzyl ester

Produkt 1

HCID 131712662Z-Gln-Trp-OBzl

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In 500 ml of THF is dissolved 50.0 g of H-Trp-OBzl. p-toluenesulfonate, and under ice-cooling, 15.4 ml of TEA, 28.0 g of Z-Gln-OH, 19.7 g of HONB and 22.7 g of DCC are added. The mixture is stirred for 15 hours. The precipitated DCU is filtered off, the filtrate concentrated and the residue dissolved in 300 ml of ethyl acetate. The solution is washed with saturated aqueous sodium hydrogen carbonate (150 ml×2), 10% aqueous citric acid (150 ml×2) and water (150 ml×2) in the order mentioned. The solvent is distilled off under reduced pressure, the residue dissolved in 300 ml of THF and the insolubles are filtered off. The filtrate is concentrated and precipitated with 500 ml of diethyl ether. The resultant powders are collected by filtration and recrystallized from acetonitrile. Yield 46.1 g (82.8%); [α]D23 +5.8°(c=1.0, DMF); Rf1 =0.60.

Aufarbeitung

  1. filtrationThe precipitated DCU is filtered off
  2. concentrationthe filtrate concentrated
  3. dissolutionthe residue dissolved in 300 ml of ethyl acetate
  4. washThe solution is washed with saturated aqueous sodium hydrogen carbonate (150 ml×2), 10% aqueous citric acid (150 ml×2) and water (150 ml×2) in the order
  5. distillationThe solvent is distilled off under reduced pressure
  6. dissolutionthe residue dissolved in 300 ml of THF
  7. filtrationthe insolubles are filtered off
  8. concentrationThe filtrate is concentrated
  9. customprecipitated with 500 ml of diethyl ether
  10. filtrationThe resultant powders are collected by filtration
  11. customrecrystallized from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-e7d34bca021c4b7791bce6297ca14fc3
Quelldatensatz
uspto-grants-1982_01
Patentnummer
US04312943

Verknüpfte Notizen

Wird geladen…