Thioacetic acid → HCID 57011249, Verbindung

HRID 37255

Reaktionsgleichung

Reaktionsgleichung von HRID 37255
[H-].[Na+].[C:3]([SH:6])(=[O:5])[CH3:4].[H][H].[NH2:9][C:10]1[S:11][CH:12]=[C:13]([C@@H:15]2[CH2:19][C@@H:18](OS(C)(=O)=O)[CH2:17][N:16]2[C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=2)=[O:26])[N:14]=1>CN(C)C=O.O.C(OCC)(=O)C>[C:3]([S:6][C@@H:18]1[CH2:17][N:16]([C:25]([O:27][CH2:28][C:29]2[CH:30]=[CH:31][C:32]([N+:35]([O-:37])=[O:36])=[CH:33][CH:34]=2)=[O:26])[C@H:15]([C:13]2[N:14]=[C:10]([NH2:9])[S:11][CH:12]=2)[CH2:19]1)(=[O:5])[CH3:4]

Komponenten

8

Edukt 4

HCID 10484Thioacetic acidHCID 24758Sodium hydrideHCID 14305071(2S,4R)-2-(2-aminothiazol-4-yl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 57011249HCID 57011249, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a suspension of sodium hydride (62.8% dispersion in mineral oil, 285 mg) in N,N-dimethylformamide (30 ml) was added thioacetic S-acid (0.54 ml) at 0°-5° C. under an atmosphere of nitrogen. After evolution of hydrogen ceased, the mixture was stirred at room temperature, and (2S, 4R) -2-(2-aminothiazol-4-yl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl) pyrrolidine (1.6 g) in N,N-dimethylformamide (20 ml) was added thereto. The mixture was stirred at 90° C. for 5 hours and poured into a mixture of ethyl acetate (100 ml) and water (100 ml). The aqueous layer was separated and extracted twice with ethyl acetate (50 ml). The organic layers were combined, washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (60 g) eluting with a mixture of acetone and dichloromethane (1:5 V/V) to give (2S, 4S)-4-acetylthio-2-(2 -aminothiazol-4-yl)-1-(4-nitrobenzyloxycarbonyl) pyrrolidine (1.26 g).

Aufarbeitung

  1. stirringThe mixture was stirred at 90° C. for 5 hours
  2. customThe aqueous layer was separated
  3. extractionextracted twice with ethyl acetate (50 ml)
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give a syrup
  8. washeluting with a mixture of acetone and dichloromethane (1:5 V/V)

Quellen und Nachweise

ORD-Eintrag
ord-9c8c130ecc234cd3aa600663a6ddb82d
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05420122

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