N-benzyloxycarbonyl-beta-benzyl-L-aspartyl-D-valine (R)-alpha-methoxymethylbenzylamide → alpha-L-aspartyl-D-valine (R)-alpha-methoxymethylbenzylamide

HRID 774

Reaktionsgleichung

[CH3:1][O:2][CH2:3][C@H:4]([NH:11][C:12](=[O:43])[C@@H:13]([CH:40]([CH3:42])[CH3:41])[NH:14][C:15](=[O:39])[C@H:16]([CH:28](CC1C=CC=CC=1)[C:29](=[O:31])[OH:30])[NH:17]C(OCC1C=CC=CC=1)=O)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CO.O.[Pd].[C]>[CH3:1][O:2][CH2:3][C@H:4]([NH:11][C:12](=[O:43])[C@@H:13]([CH:40]([CH3:41])[CH3:42])[NH:14][C:15](=[O:39])[C@H:16]([CH2:28][C:29](=[O:30])[OH:31])[NH2:17])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

To a suspension of 6.20 g (10.5 mmols) of N-benzyloxycarbonyl-β-benzyl-L-aspartyl-D-valine (R)-α-methoxymethylbenzylamide in 200 ml of methanol and 50 ml of water was added 1.50 g of 10% Pd-carbon (water content 50%). The mixture was reduced under hydrogen under heat at 40° C. The catalyst was removed by filtration, and the resulting filtrate was concentrated under reduced pressure to 15 ml. The crystal thus precipitated was removed by filtration and dried to obtain 2.69 g (7.36 mmols, 70.0% ) of α-L-aspartyl-D-valine (R)-α-methoxymethylbenzylamide.

Aufarbeitung

customThe catalyst was removed by filtration
concentrationthe resulting filtrate was concentrated under reduced pressure to 15 ml
customThe crystal thus precipitated
customwas removed by filtration
customdried

Quellen und Nachweise

ORD-Eintrag: ord-1b033c485fa54b2cb55a6e97a581a99c
Quelldatensatz: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05723165

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