Water → tert-butyl (3S,4R)-3-{[(4-chlorophenyl)carbonyl]amino}-4-(3,4-dichlorophenyl)pyrrolidine-1-carboxylate

HRID 1260943Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1260943
C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:12][C@H:13]1[C@H:17]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=2)[CH2:16][N:15]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:14]1.C(N(CC)CC)C.[Cl:40][C:41]1[CH:49]=[CH:48][C:44]([C:45](Cl)=[O:46])=[CH:43][CH:42]=1.O>C(#N)C>[Cl:40][C:41]1[CH:49]=[CH:48][C:44]([C:45]([NH:12][C@H:13]2[C@H:17]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=3)[CH2:16][N:15]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:14]2)=[O:46])=[CH:43][CH:42]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 86631350tert-butyl (3S,4R)-3-amino-4-(3,4-dichlorophenyl)pyrrolidine-1-carboxylate p-toluenesulfonate

Produkt 1

HCID 57741764tert-butyl (3S,4R)-3-{[(4-chlorophenyl)carbonyl]amino}-4-(3,4-dichlorophenyl)pyrrolidine-1-carboxylateAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of the compound (1.1 g) obtained in step 6 and triethylamine (664 μL) in acetonitrile (10 mL) was added 4-chlorobenzoyl chloride (308 μL) at 0° C., and the mixture was stirred at room temperature for 14 hr. The reaction mixture was poured into water, and the resultant product was extracted with ethyl acetate. The organic layer was washed with aqueous sodium hydrogen carbonate solution and brine and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 10→40% ethyl acetate/hexane) to give the title compound (0.80 g, 78%) as a white powder.

Aufarbeitung

  1. extractionthe resultant product was extracted with ethyl acetate
  2. washThe organic layer was washed with aqueous sodium hydrogen carbonate solution and brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 10→40% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-79093136887146f48b1912106db47a23
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08470816B2

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