Ethylmorpholine → HCID 53880215, Verbindung

HRID 1448736Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1448736
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([N:16]1[CH2:23][CH2:22][CH2:21][C@H:17]1[C:18]([OH:20])=O)=[O:15])[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1CCOCC1)C.ClC(OCC(C)C)=O.[CH:40]1([NH2:46])[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1>O1CCCC1>[CH:40]1([NH:46][C:18](=[O:20])[C@@H:17]2[CH2:21][CH2:22][CH2:23][N:16]2[C:14](=[O:15])[C@H:12]([CH3:13])[NH:11][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1

Komponenten

6

Edukt 4

HCID 7525EthylmorpholineHCID 7965CyclohexylamineHCID 62365Isobutyl chloroformateHCID 5388928Z-Ala Prolinal

Produkt 1

HCID 53880215HCID 53880215, VerbindungAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

3.2 g (0.01 mol) of N-benzyloxycarbonyl-L-alanyl-L-proline were dissolved in 50 ml of dry tetrahydrofuran and the solution was cooled to -10° C. 1.27 ml (0.01 mol) of N-ethylmorpholine were added followed by 1.31 ml (0.01 mol) of isobutyl chloroformate and the solution was stirred at -10° C. for 20 minutes. 1.21 ml (0.01 mol) of cyclohexylamine were then added and the mixture was stirred at 0° C. for 1 hour and then left to stand at room temperature for 16 hours. The mixture was evaporated and the residue was treated with 100 ml of ethyl acetate, washed with 80 ml of 1-N hydrochloric acid, 80 ml of water and 80 ml of 5% sodium bicarbonate solution, dried over sodium sulphate and evaporated to an oil. The product crystallised from ethyl acetate/ethyl to yield 2.36 g of N-benzyloxycarbonyl-L-alanyl-L-proline cyclohexylamide of melting point 130.5°-131.5° C. A second crop (0.95 g; melting point 130.5°-131.5° C.) was obtained on leaving the mother liquor to stand overnight. The total yield was 83%, [α]D20 =-96.3° (c=1.175% in methanol).

Aufarbeitung

  1. stirringthe mixture was stirred at 0° C. for 1 hour
  2. waitleft
  3. waitto stand at room temperature for 16 hours
  4. customThe mixture was evaporated
  5. additionthe residue was treated with 100 ml of ethyl acetate
  6. washwashed with 80 ml of 1-N hydrochloric acid, 80 ml of water and 80 ml of 5% sodium bicarbonate solution
  7. dry with materialdried over sodium sulphate
  8. customevaporated to an oil
  9. customThe product crystallised from ethyl acetate/ethyl

Quellen und Nachweise

ORD-Eintrag
ord-583078fc010043279ffa71e797168efb
Quelldatensatz
uspto-grants-1980_02
Patentnummer
US04187216

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