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Trifluoroacetic acid → (2S,4S)-2-(3-Dimethylaminoazetidin-1-ylcarbonyl)-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 727730
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 727730
[CH3:1][N:2]([CH3:37])[CH:3]1[CH2:6][N:5]([C:7]([C@@H:9]2[CH2:13][C@H:12]([S:14]CC3C=CC(OC)=CC=3)[CH2:11][N:10]2[C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=2)=[O:25])=[O:8])[CH2:4]1.FC(F)(F)C(O)=O.FC(F)(F)S(O)(=O)=O>C1(OC)C=CC=CC=1>[CH3:1][N:2]([CH3:37])[CH:3]1[CH2:4][N:5]([C:7]([C@@H:9]2[CH2:13][C@H:12]([SH:14])[CH2:11][N:10]2[C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=2)=[O:25])=[O:8])[CH2:6]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 56989360(2S,4S)-2-(3-dimethylaminoazetidin-1-ylcarbonyl)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Produkt 1

HCID 57145492(2S,4S)-2-(3-Dimethylaminoazetidin-1-ylcarbonyl)-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidineAusbeute 88,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7519AnisoleLösungsmittel

Versuchsvorschrift

1.47 g of (2S,4S)-2-(3-dimethylaminoazetidin-1-ylcarbonyl)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine [prepared as described in step (a) above] were dissolved in 3.02 ml of anisole, and 10.71 ml of trifluoroacetic acid and 0.488 ml of trifluoromethanesulfonic acid were added to the resulting solution, after which the mixture was stirred at the same temperature for 1 hour. The solvent was then removed by distillation under reduced pressure, and the residue was washed by repeated decantation, in turn, with hexane and with diethyl ether. Ethyl acetate was added to the residue and the mixture was made alkaline by the addition of a saturated aqueous solution of sodiumhydrogencarbonate. The ethyl acetate layer was separated, washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, to give 1.01 g of the title compound as a powder.

Aufarbeitung

  1. customThe solvent was then removed by distillation under reduced pressure
  2. washthe residue was washed
  3. additionEthyl acetate was added to the residue
  4. additionby the addition of a saturated aqueous solution of sodiumhydrogencarbonate
  5. customThe ethyl acetate layer was separated
  6. washwashed with an aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was then removed by distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6e0db24501f140df8082f9433467e3d7
Quelldatensatz
uspto-grants-1998_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05712267

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