Ethylmorpholine → Z-Val-Tyr(But)-OBut

HRID 904961

Reaktionsgleichung

Reaktionsgleichung von HRID 904961
C(N1CCOCC1)C.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:24][C@H:25]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:29][CH:28]=1.[NH:45]([C:53]([O:55][CH2:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)=[O:54])[C@H:46]([C:50](O)=[O:51])[CH:47]([CH3:49])[CH3:48].ON1C2C=CC=CC=2N=N1>CN(C)C=O>[NH:45]([C:53]([O:55][CH2:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)=[O:54])[C@H:46]([C:50]([NH:24][C@H:25]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:26][C:27]1[CH:28]=[CH:29][C:30]([O:33][C:34]([CH3:37])([CH3:35])[CH3:36])=[CH:31][CH:32]=1)=[O:51])[CH:47]([CH3:49])[CH3:48]

Komponenten

7

Edukt 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 726987N-Carbobenzoxy-L-valineHCID 7350495Tert-butyl (2S)-2-amino-3-[4-(tert-butoxy)phenyl]propanoate

Produkt 1

HCID 131713283Z-Val-Tyr(But)-OBut

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

13 ml (approx. 0.1 mole) of N-ethylmorpholine and 22 g (107 mmoles) of dicyclohexylcarbodiimide are added at 0° C. to a solution in 150 ml of dimethylformamide of 33 g (0.1 mole) of H-Tyr(But)-OBut, 25.1 g (0.1 mole) of Z-Val-OH and 13.5 g of 1-hydroxybenzotriazole. The mixture is stirred for one hour at 0° C. and allowed to stand overnight at room temperature. The precipitate is filtered off and the filtrate is concentrated. The residue is partitioned between 300 ml of ethyl acetate and 300 ml of water. The ethyl acetate phase is extracted by shaking successively with 100 ml of saturated NaHCO3 solution, 100 ml of KHSO4 /K2SO4 solution, 100 ml of saturated NaHCO3 solution and 100 ml of water. After drying over Na2SO4 the solution is concentrated. The residue is triturated with petroleum ether, cooled and filtered off. Yield 31.2 g (60%), melting point 82°-83°, [α]D21 =-20.9° (c=1, methanol).

Aufarbeitung

  1. waitto stand overnight at room temperature
  2. filtrationThe precipitate is filtered off
  3. concentrationthe filtrate is concentrated
  4. customThe residue is partitioned between 300 ml of ethyl acetate and 300 ml of water
  5. extractionThe ethyl acetate phase is extracted
  6. stirringby shaking successively with 100 ml of saturated NaHCO3 solution, 100 ml of KHSO4 /K2SO4 solution, 100 ml of saturated NaHCO3 solution and 100 ml of water
  7. dry with materialAfter drying over Na2SO4 the solution
  8. concentrationis concentrated
  9. customThe residue is triturated with petroleum ether
  10. temperaturecooled
  11. filtrationfiltered off
  12. customYield 31.2 g (60%), melting point 82°-83°, [α]D21 =-20.9° (c=1, methanol)

Quellen und Nachweise

ORD-Eintrag
ord-05bbf4852bd54c4f8f5d82550b654830
Quelldatensatz
uspto-grants-1983_12
Patentnummer
US04420424

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