4-Fluorophenyl chloroformate → rac-{(3S,4R)-4-(3,4-dichloro-phenyl)-1-[1-(1-methyl cyclopropanecarbonyl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-isobutyl-carbamic acid 4-fluoro-phenyl ester

HRID 527477

Reaktionsgleichung

Reaktionsgleichung von HRID 527477
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@H:13]([NH:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:12][N:11]([C:19]([CH:21]3[CH2:26][CH2:25][N:24]([C:27]([C:29]4([CH3:32])[CH2:31][CH2:30]4)=[O:28])[CH2:23][CH2:22]3)=[O:20])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl[C:34]([O:36][C:37]1[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=1)=[O:35]>>[F:43][C:40]1[CH:41]=[CH:42][C:37]([O:36][C:34](=[O:35])[N:14]([C@H:13]2[C@H:9]([C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)[CH2:10][N:11]([C:19]([CH:21]3[CH2:26][CH2:25][N:24]([C:27]([C:29]4([CH3:32])[CH2:30][CH2:31]4)=[O:28])[CH2:23][CH2:22]3)=[O:20])[CH2:12]2)[CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:38][CH:39]=1

Komponenten

3

Edukt 2

HCID 27332564-Fluorophenyl chloroformateHCID 67237763rac-[(3R,4S)-3-(3,4-Dichloro-phenyl)-4-isobutylamino-pyrrolidin-1-yl]-[1-(1-methyl-cyclopropanecarbonyl)-piperidin-4-yl]-methanone

Produkt 1

HCID 53247233rac-{(3S,4R)-4-(3,4-dichloro-phenyl)-1-[1-(1-methyl cyclopropanecarbonyl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-isobutyl-carbamic acid 4-fluoro-phenyl ester

Versuchsvorschrift

In analogy to the procedure described for the synthesis of example 1 (step h), the title compound rac-{(3S,4R)-4-(3,4-dichloro-phenyl)-1-[1-(1-methyl cyclopropanecarbonyl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-isobutyl-carbamic acid 4-fluoro-phenyl ester was prepared from rac-[(3R,4S)-3-(3,4-Dichloro-phenyl)-4-isobutylamino-pyrrolidin-1-yl]-[1-(1-methyl-cyclopropanecarbonyl)-piperidin-4-yl]-methanone instead of rac-{4-[(3S,4R)-3-(3,4-dichloro-phenyl)-4-methylamino-pyrrolidine-1-carbonyl]piperidin-1-yl}-(1-methyl-cyclopropyl)-methanone using 4-fluorophenyl chloroformate and was obtained as a colorless foam. MS m/e: 618.5 [M]+.

Aufarbeitung

  1. customIn analogy to the procedure described for the synthesis of example 1 (step h)
  2. customwas obtained as a colorless foam

Quellen und Nachweise

ORD-Eintrag
ord-3735b8ad500141ce8b60ebabae73c810
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346786B2

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