HCID 53991841, Verbindung → (R)-1-[[4-[2-[(R)-2-carboxy-4,4-difluoropyrrolidin-1-yl]-2-oxo-ethyl]-phenyl]-acetyl]-4,4-difluoropyrrolidine-2-carboxylic acid

HRID 1385793Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1385793
C([O:8][C:9]([C@H:11]1[CH2:15][C:14]([F:17])([F:16])[CH2:13][N:12]1[C:18](=[O:46])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27]([N:29]2[CH2:33][C:32]([F:35])([F:34])[CH2:31][C@@H:30]2[C:36]([O:38]CC2C=CC=CC=2)=[O:37])=[O:28])=[CH:22][CH:21]=1)=[O:10])C1C=CC=CC=1>C(O)C.[Pd]>[C:9]([C@H:11]1[CH2:15][C:14]([F:16])([F:17])[CH2:13][N:12]1[C:18](=[O:46])[CH2:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:26][C:27]([N:29]2[CH2:33][C:32]([F:35])([F:34])[CH2:31][C@@H:30]2[C:36]([OH:38])=[O:37])=[O:28])=[CH:24][CH:25]=1)([OH:10])=[O:8]

Komponenten

4

Edukt 1

HCID 53991841HCID 53991841, Verbindung

Produkt 1

HCID 54227571(R)-1-[[4-[2-[(R)-2-carboxy-4,4-difluoropyrrolidin-1-yl]-2-oxo-ethyl]-phenyl]-acetyl]-4,4-difluoropyrrolidine-2-carboxylic acidAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

0.64 g (0.001 mol) (R)-1-[[4-[2-[(R)-2-Benzyloxycarbonyl-4,4-difluoropyrrolidin-1-yl]-2-oxo-ethyl]-phenyl]-acetyl]-4,4-difluoropyrrolidine-2-carboxylic acid benzyl ester in 20 ml ethanol were hydrogenated at room temperature and atmospheric pressure in the presence of 0.13 g 5% palladium/carbon. After completion of the reaction the catalyst was filtered off, the solvent was distilled off, and the residue was dissolved in dichloromethane. Evaporation gave 0.28 g (61%) (R)-1-[[4-[2-[(R)-2-carboxy-4,4-difluoropyrrolidin-1-yl]-2-oxo-ethyl]-phenyl]-acetyl]-4,4-difluoropyrrolidine-2-carboxylic acid as a light yellow foam. ISP-MS: 478 (MNH4)+; [α]D=+50.3° (c=0.33% in dimethylsulfoxide).

Aufarbeitung

  1. customwere hydrogenated at room temperature
  2. customAfter completion of the reaction the catalyst
  3. filtrationwas filtered off
  4. distillationthe solvent was distilled off
  5. dissolutionthe residue was dissolved in dichloromethane
  6. customEvaporation

Quellen und Nachweise

ORD-Eintrag
ord-60cb7e990439409c99f1a3dd5d220c71
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06262089B1

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