Ethylmorpholine → Z-Ile-Phe-OBut

HRID 904956

Reaktionsgleichung

Reaktionsgleichung von HRID 904956
C(N1CCOCC1)C.[NH:9]([C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[C@H:10]([C:15]([OH:17])=O)[C@H:11]([CH2:13][CH3:14])[CH3:12].[NH2:28][C@H:29]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C)C=O>[NH:9]([C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[C@H:10]([C:15]([NH:28][C@H:29]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:17])[C@H:11]([CH2:13][CH3:14])[CH3:12]

Komponenten

7

Edukt 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 2724772N-[(Phenylmethoxy)carbonyl]-L-isoleucineHCID 6931633tert-butyl (2S)-2-amino-3-phenylpropanoate

Produkt 1

HCID 131713277Z-Ile-Phe-OBut

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1.3 ml of N-ethylmorpholine are added to the solution of 2.65 g of Z-Ile-OH, 2.58 g of H-Phe-OBut and 1.35 g of HOBt in 30 ml of dimethylformamide and 2.2 g of DCC are added to 0° C. The mixture is allowed to stand for 1 hour at 0° C. and overnight at room temperature. On the following day the precipitate is filtered off and the filtrate is concentrated. The residue is partitioned between ethyl acetate and water. The ethyl acetate phase is extracted by shaking with 20 ml of saturated NaHCO3 solution, 20 ml of K2SO4 /KHSO4 solution and 20 ml of NaHCO3 solution and is dried over Na2SO4 and concentrated. The product crystallizes from petroleum ether. Yield 3.7 g, melting point 122°-125°.

Aufarbeitung

  1. additionare added to 0° C
  2. filtrationOn the following day the precipitate is filtered off
  3. concentrationthe filtrate is concentrated
  4. customThe residue is partitioned between ethyl acetate and water
  5. extractionThe ethyl acetate phase is extracted
  6. dry with materialis dried over Na2SO4
  7. concentrationconcentrated
  8. customThe product crystallizes from petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-a9eaf38e2fd04680b6ed72562a431c04
Quelldatensatz
uspto-grants-1983_12
Patentnummer
US04420424

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