2,6-Dichlorobenzoic acid → N-[(1-methyl-3-isobutyl-indole-2-cabonyl)leucinyl]-3-amino-5-(2,6-dichlorobenzoyl) oxy-4-oxo pentanoic acid, tert-butyl ester

HRID 2297057Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2297057
[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]([NH:17][C@H:18]([C:23]([NH:25][CH:26]([C:35](=[O:38])[CH2:36]Br)[CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[O:24])[CH2:19][CH:20]([CH3:22])[CH3:21])=[O:16].[F-].[K+].[Cl:41][C:42]1[CH:50]=[CH:49][CH:48]=[C:47]([Cl:51])[C:43]=1[C:44]([OH:46])=[O:45].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]([NH:17][C@H:18]([C:23]([NH:25][CH:26]([C:35](=[O:38])[CH2:36][O:46][C:44](=[O:45])[C:43]1[C:42]([Cl:41])=[CH:50][CH:49]=[CH:48][C:47]=1[Cl:51])[CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[O:24])[CH2:19][CH:20]([CH3:22])[CH3:21])=[O:16]

Komponenten

6

Edukt 4

HCID 57582,6-Dichlorobenzoic acidHCID 522689Potassium FluorideHCID 21226206Ethyl acetate hexaneHCID 86756364N-[(1-methyl-3-isobutyl-indole-2-cabonyl)leucinyl]-3-amino-5-bromo-4-oxo-pentanoic acid, tert-butyl ester

Produkt 1

HCID 86756362N-[(1-methyl-3-isobutyl-indole-2-cabonyl)leucinyl]-3-amino-5-(2,6-dichlorobenzoyl) oxy-4-oxo pentanoic acid, tert-butyl esterAusbeute 100,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The titled product (63 mg, 100%, white solid) was prepared as described in Example 82 using N-[(1-methyl-3-isobutyl-indole-2-cabonyl)leucinyl]-3-amino-5-bromo-4-oxo-pentanoic acid, tert-butyl ester (52.9 mg, 0.089 mmol), potassium fluoride (13.0 mg, 0.22 mmol), and 2,6-dichlorobenzoic acid (17.1 mg, 0.089 mmol) in DMF (2.0 ml). TLC (hexane/EtOAc, 50/50): Rf=0.39.

Quellen und Nachweise

ORD-Eintrag
ord-cf9653f4b2b34b61bf45b560df959356
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06489353B2

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