Dicyclohexylcarbodiimide → HCID 54365840, Verbindung

HRID 482774Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 482774
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:15][CH:14](O)[CH:13]2[CH2:17][CH2:18][CH2:19][CH2:20][CH:12]2[N:11]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:10]1=[O:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:15][CH2:14][CH:13]2[CH2:17][CH2:18][CH2:19][CH2:20][CH:12]2[N:11]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:10]1=[O:27])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 2

HCID 10868Dicyclohexylcarbodiimide2×HCID 54529640HCID 54529640, Verbindung

Produkt 1

HCID 54365840HCID 54365840, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 3-(S)-t-butyloxycarbonylamino-1-ethoxycarbonylmethyl-5-hydroxy-2,3,4,5,5a,6,7,8,9,9a-decahydro-1H-[1]benzazepin-2-one (2.1 g), dicyclohexylcarbodiimide (1.8 g) and cuprous chloride (0.2 g) is heated at 80° under nitrogen for 32 hours. The reaction mixture is cooled to room temperature, the residue is dissolved in methylene chloride (200 ml), washed with dilute ammonium hydroxide (2×50 ml) and water (50 ml). The organic phase is dried over sodium sulfate and evaporated to give a mixture of the desired adduct and excess dicyclohexylcarbodiimide. This mixture is dissolved in ethyl acetate (100 ml) and placed in a pressure bottle. 10% Pd/C (0.4 g) is added and the mixture hydrogenated at 3 atmospheres pressure and 40° for 16 hours. The catalyst is filtered off and the filtrate is evaporated to give 3-(S)-t-butyloxycarbonylamino-1-ethoxycarbonylmethyl-2,3,4,5,5a,6,7,8,9,9a-decahydro-1H-[1]benzazepin-2-one, used without further purification for the next synthetic step.

Aufarbeitung

  1. temperatureis heated at 80° under nitrogen for 32 hours
  2. washwashed with dilute ammonium hydroxide (2×50 ml) and water (50 ml)
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customevaporated
  5. customto give
  6. filtrationThe catalyst is filtered off
  7. customthe filtrate is evaporated

Quellen und Nachweise

ORD-Eintrag
ord-6026b9fc2d7949f8975cfd5ab2664d78
Quelldatensatz
uspto-grants-1986_03
Patentnummer
US04575503

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