Ro 31-8875 → 2-[3(S)-[(L-asparaginyl)amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-decahydro(4aS,8aS)-isoquinoline-3(S)-carboxamide

HRID 1614286Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1614286
C(OC([NH:11][C@H:12]([C:17]([NH:19][C@@H:20]([CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C@H:21]([OH:40])[CH2:22][N:23]1[C@H:32]([C:33]([NH:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:31][C@H:30]2[C@H:25]([CH2:26][CH2:27][CH2:28][CH2:29]2)[CH2:24]1)=[O:18])[CH2:13][C:14](=[O:16])[NH2:15])=O)C1C=CC=CC=1>C(O)C.[Pd]>[NH2:11][C@H:12]([C:17]([NH:19][C@@H:20]([CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C@H:21]([OH:40])[CH2:22][N:23]1[C@H:32]([C:33]([NH:35][C:36]([CH3:38])([CH3:39])[CH3:37])=[O:34])[CH2:31][C@H:30]2[C@H:25]([CH2:26][CH2:27][CH2:28][CH2:29]2)[CH2:24]1)=[O:18])[CH2:13][C:14](=[O:16])[NH2:15]

Komponenten

4

Edukt 1

HCID 453680Ro 31-8875

Produkt 1

HCID 100980232-[3(S)-[(L-asparaginyl)amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-decahydro(4aS,8aS)-isoquinoline-3(S)-carboxamideAusbeute 99,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 195 mg of 2-[3(S)-[[N-(benzyloxycarbonyl)-L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-decahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide in 20 ml of ethanol was hydrogenated at room temperature and atmospheric pressure for 18 hours over 10 mg of 10% palladium-on-charcoal. The catalyst was filtered off and the filtrate was evaporated under reduced pressure to give 154 mg of 2-[3(S)-[(L-asparaginyl)amino]2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-decahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide.

Aufarbeitung

  1. customwas hydrogenated at room temperature
  2. filtrationThe catalyst was filtered off
  3. customthe filtrate was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f14bc7487ffc4ec9b2c49e712db6ed79
Quelldatensatz
uspto-grants-1993_03
Patentnummer
US05196438

Notizen zur Reaktion

Wird geladen…