Dimethylformamide → (2r)-1-{(2s,4s)-4-Acetoxy-1-(3,3,3-triphenylpropanoyl)pyrrolidin-2-yl}carbonyl-n-{((3r)-1-cyclohexylmethyl-3-piperidyl)methyl}pyrrolidine-2-carboxamide

HRID 394025

Reaktionsgleichung

Reaktionsgleichung von HRID 394025
C1(CN2CCC[C@H](CNC(C[C@H:19]3[CH2:23][CH2:22][CH2:21][N:20]3[C:24]([C@@H:26]3[CH2:30][C@@H:29]([O:31]S(C)(=O)=O)[CH2:28][N:27]3[C:36](=[O:57])[CH2:37][C:38]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[O:25])=O)C2)CCCCC1.[CH3:58][N:59]([CH3:62])[CH:60]=O>C([O-])(=O)C.C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[C:29]([O:31][C@@H:29]1[CH2:28][N:27]([C:36](=[O:57])[CH2:37][C:38]([C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)([C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C@H:26]([C:24]([N:20]2[CH2:21][CH2:22][CH2:23][C@@H:19]2[C:24]([NH:20][CH2:19][C@H:23]2[CH2:22][CH2:21][CH2:60][N:59]([CH2:62][CH:39]3[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]3)[CH2:58]2)=[O:25])=[O:25])[CH2:30]1)(=[O:31])[CH3:28]

Komponenten

5

Edukt 2

HCID 6228DimethylformamideHCID 131724629(2R)-N-{((3R)-1-cyclohexylmethyl-3-piperidyl)methyl}-1-{(2S,4R)-4-(methylsulfonyloxy)-1-(3,3,3-triphenylpropanoyl)pyrrolidin-2-yl}carbonylpyrrolidine-2-carboxyamide

Produkt 1

HCID 12149972(2r)-1-{(2s,4s)-4-Acetoxy-1-(3,3,3-triphenylpropanoyl)pyrrolidin-2-yl}carbonyl-n-{((3r)-1-cyclohexylmethyl-3-piperidyl)methyl}pyrrolidine-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 82707Tetrabutylammonium AcetateKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 40 mg of (2R)-N-{((3R)-1-cyclohexylmethyl-3-piperidyl)methyl}-1-{(2S,4R)-4-(methylsulfonyloxy)-1-(3,3,3-triphenylpropanoyl)pyrrolidin-2-yl}carbonylpyrrolidine-2-carboxyamide and 30 mg of tetrabutylammonium acetate in 1 ml of N,N-dimethylformamide was stirred at 85° C. for 15 hours under heating. The reaction liquid was diluted with ethyl acetate, successively washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified with a preparative thin-layer chromatography (Kieselgel™ 60F254, Art. 5744 (Merck), chloroform/methanol/28% aqueous ammonia=100/8/1), to provide 14 mg of the title compound as a colorless oily substance.

Aufarbeitung

  1. temperatureunder heating
  2. customThe reaction liquid
  3. washsuccessively washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified with a preparative thin-layer chromatography (Kieselgel™ 60F254, Art. 5744 (Merck), chloroform/methanol/28% aqueous ammonia=100/8/1)

Quellen und Nachweise

ORD-Eintrag
ord-8ce7075e514b496193cfb7e61b49b8a1
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809108B1

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