Succinamic acid → rac-[(3R,4S)-1-(3-carbamoyl-propionyl)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester

HRID 587330

Reaktionsgleichung

Reaktionsgleichung von HRID 587330
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:25])[N:10]([C@@H:12]2[C@@H:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=3)[CH2:15][NH:14][CH2:13]2)[CH3:11])=[CH:4][CH:3]=1.[C:26](O)(=[O:32])[CH2:27][CH2:28][C:29]([NH2:31])=[O:30]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:25])[N:10]([C@@H:12]2[C@@H:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=3)[CH2:15][N:14]([C:26](=[O:32])[CH2:27][CH2:28][C:29](=[O:30])[NH2:31])[CH2:13]2)[CH3:11])=[CH:4][CH:3]=1

Komponenten

3

Edukt 2

HCID 12522Succinamic acidHCID 67234230rac-[(3R,4S)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester

Produkt 1

HCID 58302995rac-[(3R,4S)-1-(3-carbamoyl-propionyl)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester

Versuchsvorschrift

In analogy to the procedure described for the synthesis of example 44 (step c), the title compound rac-[(3R,4S)-1-(3-carbamoyl-propionyl)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester was prepared from rac-[(3R,4S)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester instead of rac-{4-[(3S,4R)-3-(3,4-dichloro-phenyl)-4-methylamino-pyrrolidine-1-carbonyl]-piperidin-1-yl}-(1-methyl-cyclopropyl)-methanone using succinamic acid instead of 1-methylcyclopropane-1-carboxylic acid and was obtained as a colorless oil. MS m/e: 465.1 [M]+.

Aufarbeitung

  1. customIn analogy to the procedure described for the synthesis of example 44 (step c)
  2. customwas obtained as a colorless oil

Quellen und Nachweise

ORD-Eintrag
ord-b7a9e3c85d0f44af825da7e67368fcd2
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09226916B2

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