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Ethyl Acetate → (2S,4R)-4-methanesulfonyloxy-2-[N-(N,N-dimethylaminomethylene) carbamoyl]-1-(4-nitrobenzyloxycarbonyl) pyrrolidine

HRID 1649804
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1649804
[C:1]([C@@H:4]1[CH2:8][C@@H:7]([O:9][S:10]([CH3:13])(=[O:12])=[O:11])[CH2:6][N:5]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)=[O:15])(=[O:3])[NH2:2].CO[CH:29](OC)[N:30]([CH3:32])[CH3:31].C(OCC)(=O)C>ClCCl>[CH3:13][S:10]([O:9][C@H:7]1[CH2:6][N:5]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)=[O:15])[C@H:4]([C:1](=[O:3])[N:2]=[CH:29][N:30]([CH3:32])[CH3:31])[CH2:8]1)(=[O:11])=[O:12]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 78373Dimethylformamide dimethyl acetalHCID 13455346trans-1-(p-nitrobenzyloxycarbonyl)-4-methanesulfonyloxy-L-prolineamide

Produkt 1

HCID 57094384(2S,4R)-4-methanesulfonyloxy-2-[N-(N,N-dimethylaminomethylene) carbamoyl]-1-(4-nitrobenzyloxycarbonyl) pyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To (2S,4R)-2-carbamoyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (3 g) was added N,N-dimethylformamide dimethylacetal (3 ml) and the mixture was stirred at 120° C. for 1 hour. The mixture was poured into a mixture of ethyl acetate and dichloromethane, washed with water and brine successively, and evaporated in vacuo to give (2S,4R)-4-methanesulfonyloxy-2-[N-(N,N-dimethylaminomethylene)carbamoyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine. The compound obtained above was dissolved in acetic acid (30 ml) and to this solution was added hydrazine hydrate (0.36 ml) at room temperature. After stirring at the same temperature for 2 hours, the mixture was poured into water and ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate and brine successively, dried over magnesium sulfate, and evaporated in vacuo. The oily residue was subjected to a column chromatography on silica gel (90 g) eluting with a mixture of methanol and dichloromethane (1:20 V/V) to give (2S,4R)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)-2-(1H-1,2,4-triazol-3-yl)pyrrolidine (1.5 g).

Aufarbeitung

  1. washwashed with water and brine successively
  2. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7b932078dfcd4e8e832dcb0ba2ca3de5
Quelldatensatz
uspto-grants-1990_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04921852

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