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 45622

Reaktionsgleichung

Reaktionsgleichung von HRID 45622
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-c5c4efe93d3946e0893ac25a23b38fcc
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541579B2

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