2,3,5,6-Tetrafluorophenol → N-[(1-methyl-3-isobutyl-indole-2-cabonyl)cyclohexylalaninyl]-3-amino-4-oxo-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl ester

HRID 634940

Reaktionsgleichung

Reaktionsgleichung von HRID 634940
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][CH:12]([CH3:14])[CH3:13])=[C:3]1[C:15]([N:17]([CH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1)[C@H:18]([C:20]([NH:22][CH:23]([C:32](=[O:35])[CH2:33]Br)[CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[O:21])[CH3:19])=[O:16].[F-].[K+].[F:44][C:45]1[C:50]([F:51])=[CH:49][C:48]([F:52])=[C:47]([F:53])[C:46]=1[OH:54].CCCCCC.CCOC(C)=O>CN(C=O)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][CH:12]([CH3:14])[CH3:13])=[C:3]1[C:15]([N:17]([CH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1)[C@H:18]([C:20]([NH:22][CH:23]([C:32](=[O:35])[CH2:33][O:54][C:46]1[C:47]([F:53])=[C:48]([F:52])[CH:49]=[C:50]([F:51])[C:45]=1[F:44])[CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[O:21])[CH3:19])=[O:16]

Komponenten

6

Edukt 4

HCID 698582,3,5,6-TetrafluorophenolHCID 522689Potassium FluorideHCID 21226206Ethyl acetate hexaneHCID 86756366N-[(1-methyl-3-isobutyl-indole-2-cabonyl)cyclohexylalaninyl]-3-amino-5-bromo-4-oxo-pentanoic acid, tert-butyl ester

Produkt 1

HCID 86756365N-[(1-methyl-3-isobutyl-indole-2-cabonyl)cyclohexylalaninyl]-3-amino-4-oxo-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The titled product was prepared as described in Example 82 using N-[(1-methyl-3-isobutyl-indole-2-carbonyl)cyclohexylalaninyl]-3-amino-5-bromo-4-oxo-pentanoic acid, tert-butyl ester (50.8 mg, 0.08 mmol), potassium fluoride (12.0 mg, 0.21 mmol), and 2,3,5,6-tetrafluorophenol (13.3 mg, 0.08 mmol) in DMF (2.0 ml). TLC (hexane/EtOAc, 3/1): Rf=0.25.

Quellen und Nachweise

ORD-Eintrag
ord-96643832e51949ff81e8b303e1c84318
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06184244B2

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