Cycloheptylamine → HCID 54187700, Verbindung

HRID 1448738Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1448738
[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([NH2:47])[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1>O1CCCC1>[CH:40]1([NH:47][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])[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1

Komponenten

6

Edukt 4

HCID 2899CycloheptylamineHCID 7525EthylmorpholineHCID 62365Isobutyl chloroformateHCID 5388928Z-Ala Prolinal

Produkt 1

HCID 54187700HCID 54187700, VerbindungAusbeute 67,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

6.4 g (0.02 mol) of N-benzyloxycarbonyl-L-alanyl-L-proline were dissolved in 75 ml of dry tetrahydrofuran and the solution was cooled to -10° C. 2.54 ml (0.02 mol) of N-ethylmorpholine and 2.62 ml (0.02 mol) of isobutyl chloroformate were added and the solution was stirred at -10° C. for 20 minutes. A solution of 2.25 g (0.02 mol) of cycloheptylamine in 25 ml of dry tetrahydrofuran was then added. The mixture was stirred at 0° C. for 1 hour and then left to stand at room temperature for 16 hours. The mixture was then evaporated and the residue extracted twice with 50 ml of ethyl acetate each time. The combined ethyl acetate extracts were washed successively with 1-N hydrochloric acid, water, 5% sodium bicarbonate solution and water and then dried over magnesium sulphate. Evaporation yielded an oil which solidified upon trituration with petroleum ether. The solid was recrystallised from ethyl acetate/petroleum ether to yield 5.6 g (67.5%) of N-benzyloxycarbonyl-L-alanyl-L-proline cycloheptylamide of melting point 110°-113° C.; [α]D20 =-92.4° (c=1.05% 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 then evaporated
  5. extractionthe residue extracted twice with 50 ml of ethyl acetate each time
  6. washThe combined ethyl acetate extracts were washed successively with 1-N hydrochloric acid, water, 5% sodium bicarbonate solution and water
  7. dry with materialdried over magnesium sulphate
  8. customEvaporation
  9. customyielded an oil which
  10. customThe solid was recrystallised from ethyl acetate/petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-4e837fa887c243ac8809caa72c09d010
Quelldatensatz
uspto-grants-1980_02
Patentnummer
US04187216

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