(2RS)-2-(2,4-difluorophenyl)-2-[(3R,6R)-3-(2,3-dihydro-1H-inden-2-yl)-6-isobutyl-2,5-dioxopiperazin-1-yl]-N-(2-benzyloxyphenyl)ethanamide → (2RS)-2-(2,4-difluorophenyl)-2-[(3R,6R)-3-(2,3-dihydro-1H-inden-2-yl)-6-isobutyl-2,5-dioxopiperazin-1-yl]-N-(2-hydroxyphenyl)ethanamide

HRID 45616

Reaktionsgleichung

Reaktionsgleichung von HRID 45616
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([N:27]1[C@H:32]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:31](=[O:37])[NH:30][C@H:29]([CH:38]2[CH2:46][C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH2:39]2)[C:28]1=[O:47])[C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19]CC1C=CC=CC=1)=[O:11]>C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([N:27]1[C@H:32]([CH2:33][CH:34]([CH3:35])[CH3:36])[C:31](=[O:37])[NH:30][C@H:29]([CH:38]2[CH2:46][C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH2:39]2)[C:28]1=[O:47])[C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19])=[O:11]

Komponenten

4

Edukt 1

HCID 68844683(2RS)-2-(2,4-difluorophenyl)-2-[(3R,6R)-3-(2,3-dihydro-1H-inden-2-yl)-6-isobutyl-2,5-dioxopiperazin-1-yl]-N-(2-benzyloxyphenyl)ethanamide

Produkt 1

HCID 11649656(2RS)-2-(2,4-difluorophenyl)-2-[(3R,6R)-3-(2,3-dihydro-1H-inden-2-yl)-6-isobutyl-2,5-dioxopiperazin-1-yl]-N-(2-hydroxyphenyl)ethanamideAusbeute 91,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(2RS)-2-(2,4-difluorophenyl)-2-[(3R,6R)-3-(2,3-dihydro-1H-inden-2-yl)-6-isobutyl-2,5-dioxopiperazin-1-yl]-N-(2-benzyloxyphenyl)ethanamide (3.381 g) was dissolved in ethyl acetate (200 ml) and hydrogenated at atmospheric pressure over 10% palladium on carbon catalyst (0.980 g of 10% Pd/C:water 1:1 w/w) at room temperature for five hours. The reaction mixture was filtered through Celite and the solvent was removed under reduced pressure to give the (2RS)-2-(2,4-difluorophenyl)-2-[(3R,6R)-3-(2,3-dihydro-1H-inden-2-yl)-6-isobutyl-2,5-dioxopiperazin-1-yl]-N-(2-hydroxyphenyl)ethanamide as a cream-coloured foam (2.650 g).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6a6d1bdd451244f493a413b464ab42c9
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541579B2

Verknüpfte Notizen

Wird geladen…