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p-Toluenesulfonic acid → Boc-Gly-Pro-Glu(O-But)-Gly-OMe

HRID 1461975
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1461975
[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:2][C:3]([N:5]1[CH2:12][CH2:11][CH2:10][C@H:6]1[C:7]([OH:9])=O)=[O:4].[NH2:20][C@H:21]([C:31]([NH:33][CH2:34][C:35]([O:37][CH3:38])=[O:36])=[O:32])[CH2:22][CH2:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27].S(O)(C1C=CC(C)=CC=1)(=O)=O.C(N1CCOCC1)C.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:2][C:3]([N:5]1[CH2:12][CH2:11][CH2:10][C@H:6]1[C:7]([NH:20][C@H:21]([C:31]([NH:33][CH2:34][C:35]([O:37][CH3:38])=[O:36])=[O:32])[CH2:22][CH2:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:9])=[O:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 6101p-Toluenesulfonic acidHCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 11673468Boc-gly-pro-OHHCID 13419975H-Glu(O-But)-Gly-OMe

Produkt 1

HCID 131713569Boc-Gly-Pro-Glu(O-But)-Gly-OMe

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2.7 g (10 mmoles) of Boc-Gly-Pro-OH and 4.5 g (10 mmoles) of H-Glu(O-But)-Gly-OMe.TosOH are dissolved in 20 ml of dimethylformamide. 1.28 ml (10 mmoles) of N-ethylmorpholine and 2.2 g (10.6 mmoles) of dicyclohexylcarbodiimide are added and the mixture is left to stand at room temperature overnight. The dicyclohexylurea is then filtered off, the solvent is distilled off in vacuo, the residue is taken up in ethyl acetate and the solution is washed with citric acid, bicarbonate solution and water, as described above, dried over sodium sulfate and evaporated to dryness. The residue is dissolved in ether and a precipitate is obtained with petroleum ether and filtered off.

Aufarbeitung

  1. waitthe mixture is left
  2. filtrationThe dicyclohexylurea is then filtered off
  3. distillationthe solvent is distilled off in vacuo
  4. washthe solution is washed with citric acid, bicarbonate solution and water
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. dissolutionThe residue is dissolved in ether
  8. customa precipitate is obtained with petroleum ether
  9. filtrationfiltered off

Quellen und Nachweise

ORD-Eintrag
ord-26521d3c592341729752d8aab5957ebd
Quelldatensatz
uspto-grants-1984_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04457866

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