n-(2-Fluoro-4-hydroxyphenyl)acetamide → (2S)-3-(4-Acetylamino-3-fluorophenoxy)-2-hydroxy-2-methyl-N-(3-methyl-4-nitrophenyl)propionamide

HRID 133738

Reaktionsgleichung

Reaktionsgleichung von HRID 133738
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[F:12])(=[O:3])[CH3:2].[CH3:13][C:14]1[CH:15]=[C:16]([NH:23][C:24](=[O:30])[C@:25]([OH:29])([CH3:28])[CH2:26]Br)[CH:17]=[CH:18][C:19]=1[N+:20]([O-:22])=[O:21]>>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:28][C@@:25]([OH:29])([CH3:26])[C:24]([NH:23][C:16]2[CH:17]=[CH:18][C:19]([N+:20]([O-:22])=[O:21])=[C:14]([CH3:13])[CH:15]=2)=[O:30])=[CH:7][C:6]=1[F:12])(=[O:3])[CH3:2]

Komponenten

3

Edukt 2

HCID 190616n-(2-Fluoro-4-hydroxyphenyl)acetamideHCID 59903827(2R)-3-bromo-2-hydroxy-2-methyl-N-(3-methyl-4-nitrophenyl)propionamide

Produkt 1

HCID 67526766(2S)-3-(4-Acetylamino-3-fluorophenoxy)-2-hydroxy-2-methyl-N-(3-methyl-4-nitrophenyl)propionamide

Versuchsvorschrift

(2S)-3-(4-Acetylamino-3-fluorophenoxy)-2-hydroxy-2-methyl-N-(3-methyl-4-nitrophenyl)propionamide was prepared according to the method B as described in Example 3e starting from 4-acetylamino-3-fluorophenol and N-[3-methyl-4-(nitro)phenyl]-(2R)-3-bromo-2-hydroxy-2-methylpropanamide. 1H NMR (DMSO-d6): 1.42 (3H, s), 2.02 (3H, s), 2.53 (3H, s), 3.97 (1H, d, J=9.7 Hz), 4.21 (1H, d, J=9.7 Hz), 6.23 (1H, bs), 6.72 (1H, m), 6.90 (1H, m), 7.56 (1H, m), 7.88 (1H, dd, J=9.0 Hz and 2.2 Hz), 7.93 (1H, d, J=2.2 Hz), 8.03 (1H, d, J=9.0 Hz), 9.51 (1H, s), 10.15 (1H, bs).

Quellen und Nachweise

ORD-Eintrag
ord-54a11b4223dc4a479215c80b33c67d28
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390923B2

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