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Ethylmorpholine → Z-D-Trp-D-Phe-OMe

HRID 596349
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 596349
[NH:1]([C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[C@@H:2]([C:13](O)=[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.[CH3:26][O:27][C:28]([C@H:30]([NH2:38])[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29].Cl.ON1C2C=CC=CC=2N=N1.C(N1CCOCC1)C.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C.CO.C(Cl)(Cl)Cl>[CH3:26][O:27][C:28](=[O:29])[C@@H:30]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[NH:38][C:13](=[O:14])[C@@H:2]([CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)[NH:1][C:16]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:17]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 700663N-(Benzyloxycarbonyl)-D-tryptophanHCID 11481330methyl (2R)-2-amino-3-phenylpropanoate;hydrochloride

Produkt 1

HCID 68125752Z-D-Trp-D-Phe-OMe

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 6212ChloroformLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of Z-D-Trp-OH (3.62 g, 10.7 mmoles), H-D-Phe-Ome.HCl (2.3 g, 10.7 mmoles) and 1-hydroxybenzotriazole (2.89 g, 21.4 mmoles) in dry DMF (25 ml) is cooled to 0° C and N-ethylmorpholine (1.37 ml, 10.7 mmoles) is added. A cold (0° C) solution of DCC (2.27 g, 11 mmoles) in DMF (6 ml) is added dropwise and the reaction mixture is stirred for 1 hr at 0° C and 1 hr at room temperature. The reaction mixture is then cooled to 0° C, filtered, the filtrate evaporated under reduced pressure and taken upon in EtOAc. The EtOAc solution is washed with saturated NaHCO3 solution, water, cold citric acid (2N), water, saturated NaHCO3 solution and saturated NaCl solution, dried with MgSO4, and evaporated under reduced pressure to afford the crude title product which is subjected to chromatography on a column of silica gel (500 g) with CHCl3 containing MeOH (1%) as eluent. The eluates are evaporated under reduced pressure and the residue is crystallized from EtOAc-petroleum ether to give the title compound; mp 130° - 131° C, [α]D25 = +34.1° (c = 1, DMF).

Aufarbeitung

  1. temperatureThe reaction mixture is then cooled to 0° C
  2. filtrationfiltered
  3. customthe filtrate evaporated under reduced pressure
  4. washThe EtOAc solution is washed with saturated NaHCO3 solution, water, cold citric acid (2N), water, saturated NaHCO3 solution and saturated NaCl solution
  5. dry with materialdried with MgSO4
  6. customevaporated under reduced pressure
  7. customto afford the crude title product which
  8. customThe eluates are evaporated under reduced pressure
  9. customthe residue is crystallized from EtOAc-petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-6f7a7986ca6b41c9b6d3648bf620668a
Quelldatensatz
uspto-grants-1977_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04010260

Notizen zur Reaktion

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