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Dicyclohexylcarbodiimide → Z-Sta-Sar-His-Lys(Boc)-OMe

HRID 1982330
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1982330
[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C@H:7]([CH2:9][C:10]([OH:12])=O)[OH:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[NH:23]([CH2:25][C:26]([NH:28][C@H:29]([C:36]([NH:38][C@H:39]([C:52]([O:54][CH3:55])=[O:53])[CH2:40][CH2:41][CH2:42][CH2:43][NH:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])=[O:37])[CH2:30][C:31]1[N:35]=[CH:34][NH:33][CH:32]=1)=[O:27])[CH3:24].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C.O>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C@H:7]([CH2:9][C:10]([N:23]([CH2:25][C:26]([NH:28][C@H:29]([C:36]([NH:38][C@H:39]([C:52]([O:54][CH3:55])=[O:53])[CH2:40][CH2:41][CH2:42][CH2:43][NH:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])=[O:37])[CH2:30][C:31]1[N:35]=[CH:34][NH:33][CH:32]=1)=[O:27])[CH3:24])=[O:12])[OH:8])[CH2:3][CH:4]([CH3:5])[CH3:6]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 14560231Z-Sta-OHHCID 178484730HCID 178484730, Verbindung

Produkt 1

HCID 178501444Z-Sta-Sar-His-Lys(Boc)-OMe

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

254 mg of Z-Sta-OH (see stage 1.12), 297 mg of H-Sar-His-Lys(Boc)-OMe, 97 mg of HOBt×H2O and 196 mg of DCCI are dissolved, in this sequence, in 3 ml of DMF and the whole is left to stand for 20 hours at room temperature. The DCH which has crystallised out is filtered off, the filtrate is concentrated to dryness, heated for 1 hour at 60° in 7 ml of methanol/glacial acetic acid/H2O (94:3:3), and this solution is again concentrated to dryness. The oily residue is purified by chromatography over 75 g of silica gel (Merck No. 60, 230-400 mesh) by elution with CHCl3 /MeOH (9:1). The pure fractions are dissolved in ethyl acetate, washed with NaHCO3 solution and with H2O and, by concentration of the organic phase, Z-Sta-Sar-His-Lys(Boc)-OMe is obtained in amorphous form (honey); Rf (F)=0.15; Rf (I)=0.5.

Aufarbeitung

  1. waitthe whole is left
  2. customThe DCH which has crystallised out
  3. filtrationis filtered off
  4. concentrationthe filtrate is concentrated to dryness
  5. temperatureheated for 1 hour at 60° in 7 ml of methanol/glacial acetic acid/H2O (94:3:3)
  6. concentrationthis solution is again concentrated to dryness
  7. customThe oily residue is purified by chromatography over 75 g of silica gel (Merck No. 60, 230-400 mesh) by elution with CHCl3 /MeOH (9:1)
  8. dissolutionThe pure fractions are dissolved in ethyl acetate
  9. washwashed with NaHCO3 solution and with H2O and, by concentration of the organic phase

Quellen und Nachweise

ORD-Eintrag
ord-bca7bad91e344a1c8ebbcd2e163fdf46
Quelldatensatz
uspto-grants-1986_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04595677

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