2-(Dihydroxyboranyl)benzoic acid → 3'-Chloro-4'-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(4-methyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-propyl]-biphenyl-2-carboxylic acid

HRID 2386717

Reaktionsgleichung

Reaktionsgleichung von HRID 2386717
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:27])[C:9]([C:15]2[CH:16]=[CH:17][C:18]3[O:23][CH2:22][C:21](=[O:24])[N:20]([CH3:25])[C:19]=3[CH:26]=2)([OH:14])[C:10]([F:13])([F:12])[F:11])=[C:4]([Cl:28])[CH:3]=1.[C:29]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1B(O)O)([OH:31])=[O:30]>>[Cl:28][C:4]1[CH:3]=[C:2]([C:33]2[C:32]([C:29]([OH:31])=[O:30])=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:7]=[CH:6][C:5]=1[CH:8]([CH3:27])[C:9]([OH:14])([C:15]1[CH:16]=[CH:17][C:18]2[O:23][CH2:22][C:21](=[O:24])[N:20]([CH3:25])[C:19]=2[CH:26]=1)[C:10]([F:13])([F:12])[F:11]

Komponenten

3

Edukt 2

HCID 27339852-(Dihydroxyboranyl)benzoic acidHCID 666971866-[2-(4-Bromo-2-chloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-4-methyl-4H-benzo[1,4]oxazin-3-one

Produkt 1

HCID 666973533'-Chloro-4'-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(4-methyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-propyl]-biphenyl-2-carboxylic acid

Versuchsvorschrift

In analogy to Example 17, step 2, 6-[2-(4-bromo-2-chloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-4-methyl-4H-benzo[1,4]oxazin-3-one (Example 22, step 3) was reacted with 2-carboxyphenylboronic acid to give the title compound as an off-white solid. MS (m/e, ISP neg. ion)=518.2 [M−H+].

Quellen und Nachweise

ORD-Eintrag
ord-0b7371e8b4854320a0cc3539973ca8dd
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08268820B2

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