methyl (2S)-2-[[(1R)-1-(1-benzofuran-5-yl)-2-oxo-2-(2-phenylmethoxyanilino)ethyl]amino]-4-methylpentanoate → methyl N-{(1R)-1-(benzofuran-5-yl)-2-[(2-hydroxyphenyl)amino]-2-oxoethyl}-L-leucinate

HRID 2108706

Reaktionsgleichung

Reaktionsgleichung von HRID 2108706
C([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:37])[C@H:17]([NH:27][C@H:28]([C:33]([O:35][CH3:36])=[O:34])[CH2:29][CH:30]([CH3:32])[CH3:31])[C:18]1[CH:19]=[CH:20][C:21]2[O:25][CH:24]=[CH:23][C:22]=2[CH:26]=1)C1C=CC=CC=1>[Pd].C(OCC)(=O)C>[O:25]1[C:21]2[CH:20]=[CH:19][C:18]([C@@H:17]([NH:27][C@H:28]([C:33]([O:35][CH3:36])=[O:34])[CH2:29][CH:30]([CH3:31])[CH3:32])[C:16]([NH:15][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[OH:8])=[O:37])=[CH:26][C:22]=2[CH:23]=[CH:24]1

Komponenten

4

Edukt 1

HCID 45076860methyl (2S)-2-[[(1R)-1-(1-benzofuran-5-yl)-2-oxo-2-(2-phenylmethoxyanilino)ethyl]amino]-4-methylpentanoate

Produkt 1

HCID 45076859methyl N-{(1R)-1-(benzofuran-5-yl)-2-[(2-hydroxyphenyl)amino]-2-oxoethyl}-L-leucinateAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of palladium on carbon (10%, 500 mg), methyl N-[(1R)-2-{[2-(benzyloxy)phenyl]amino}-1-(benzofuran-5-yl)-2-oxoethyl]-L-leucinate (5.1 g) and ethyl acetate (60 ml) was stirred under a hydrogen atmosphere for 5 hours. The reaction was then filtered through Celite and the filter pad was washed with further portions of ethyl acetate. The combined organic fractions were evaporated to give methyl N-{(1R)-1-(benzofuran-5-yl)-2-[(2-hydroxyphenyl)amino]-2-oxoethyl}-L-leucinate (3.429 g).

Aufarbeitung

  1. filtrationThe reaction was then filtered through Celite
  2. washthe filter pad was washed with further portions of ethyl acetate
  3. customThe combined organic fractions were evaporated

Quellen und Nachweise

ORD-Eintrag
ord-2101ddd77f0040e1ac5433ee1c280240
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07514437B2

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