Ethylmorpholine → Carbobenzyloxytryptophylserine methyl ester

HRID 1415335

Reaktionsgleichung

Reaktionsgleichung von HRID 1415335
C(N1CCOCC1)C.C1CCC(N=C=NC2CCCCC2)CC1.[NH:24]([C:39]([O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:40])[C@H:25]([C:36](O)=[O:37])[CH2:26][C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[NH:29][CH:28]=1.[CH3:49][O:50][C:51]([C@@H:53]([NH2:56])[CH2:54][OH:55])=[O:52].Cl.C1C=CC2N(O)N=NC=2C=1>O1CCCC1>[NH:24]([C:39]([O:41][CH2:42][C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)=[O:40])[C@H:25]([C:36]([NH:56][C@H:53]([C:51]([O:50][CH3:49])=[O:52])[CH2:54][OH:55])=[O:37])[CH2:26][C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[NH:29][CH:28]=1

Komponenten

7

Edukt 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 101176benzyloxycarbonyl-L-tryptophanHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)

Produkt 1

HCID 12821032Carbobenzyloxytryptophylserine methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

6.4 ml of N-ethylmorpholine and at 0° C, a solution of 10.5 g of DCC in 50 ml of tetrahydrofurane were added to a solution of 16.9 g (50 mmols) of Z-Trp-OH, 7.7 g (50 mmols) of H-Ser-OMe . HCl and 6.65 g (50 mmols) of HOBt in 100 ml of absolute tetrahydrofurane. The mixture was stirred for one hour at 0° C and for 2 hours at room temperature, the deposit was suction-filtered and the filtrate was concentrated. The residue was dissolved in ethyl acetate and successively extracted with saturated NaHCO3 -solution, KHSO4 -solution, saturated NaHCO3 -solution and water. The ethyl acetate phase was dried over Na2SO4 and concentrated. The remaining oil was dissolved in 120 ml of isopropanol. When standing in the refrigerator the substance was crystallized. Yield: 15.6 g (71%), melting point: 143° - 145° C. [α]D25 = -16.8° (c=1, dimethylacetamide)

Aufarbeitung

  1. filtrationthe deposit was suction-filtered
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. extractionsuccessively extracted with saturated NaHCO3 -solution, KHSO4 -solution, saturated NaHCO3 -solution and water
  5. dry with materialThe ethyl acetate phase was dried over Na2SO4
  6. concentrationconcentrated
  7. dissolutionThe remaining oil was dissolved in 120 ml of isopropanol
  8. customwas crystallized

Quellen und Nachweise

ORD-Eintrag
ord-767a1946880c44489768f355a9d11715
Quelldatensatz
uspto-grants-1977_01
Patentnummer
US04003884

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