Methyl acetoacetate → 5-(2-Fluoro-5-trifluoromethyl-phenyl)-2-methyl-1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-1H-pyrrole-3-carboxylic acid ((1R,2R)-2-hydroxy-cyclohexyl)-amide

HRID 229869

Reaktionsgleichung

Reaktionsgleichung von HRID 229869
CO[C:3](=[O:8])[CH2:4][C:5](=O)[CH3:6].Br[CH2:10][C:11]([C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=1[F:23])=O.[CH2:24]([NH2:30])[C@H:25]1[O:29][CH2:28][CH2:27][CH2:26]1.[NH2:31][C@@H:32]1[CH2:37][CH2:36][CH2:35][CH2:34][C@H:33]1[OH:38]>>[OH:38][C@@H:33]1[CH2:34][CH2:35][CH2:36][CH2:37][C@H:32]1[NH:31][C:3]([C:4]1[CH:10]=[C:11]([C:13]2[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=2[F:23])[N:30]([CH2:24][C@@H:25]2[CH2:26][CH2:27][CH2:28][O:29]2)[C:5]=1[CH3:6])=[O:8]

Komponenten

5

Edukt 4

HCID 7757Methyl acetoacetateHCID 641530(S)-(+)-TetrahydrofurfurylamineHCID 735777(1R,2R)-2-AminocyclohexanolHCID 27787842-Fluoro-5-(trifluoromethyl)phenacyl bromide

Produkt 1

HCID 116699505-(2-Fluoro-5-trifluoromethyl-phenyl)-2-methyl-1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-1H-pyrrole-3-carboxylic acid ((1R,2R)-2-hydroxy-cyclohexyl)-amide

Versuchsvorschrift

The title compound was synthesized in analogy to example 7, using 3-oxo-butyric acid methyl ester as compound of formula R, 2-bromo-1-[2-fluoro-5-(trifluoromethyl)-phenyl]-ethanone as compound of formula S, (S)-tetrahydrofurfurylamine as R3—(CH2)m—NH2 and (1R,2R)-2-aminocyclohexanol as R1R2NH, MS (ISP) 469.5 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-37e4ab64492d40c4b96072b351b3e123
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07563910B2

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