Potassium ethanethioate → (3S,5S)-3-Acetylthio-1-allyloxycarbonyl-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-3-yl)methyl]pyrrolidine

HRID 568264Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 568264
[C:1]([O-:4])(=[S:3])[CH3:2].[K+].[CH2:6]([O:9][C:10]([N:12]1[C@H:16]([CH:17]([OH:26])[C:18]2[N:19]3[CH:25]=[N:24][CH:23]=[C:20]3[S:21][CH:22]=2)[CH2:15][C@@H:14](OS(C)(=O)=O)[CH2:13]1)=[O:11])[CH:7]=[CH2:8]>CN(C=O)C.C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:1]([S:3][C@H:14]1[CH2:15][C@@H:16]([CH:17]([OH:26])[C:18]2[N:19]3[CH:25]=[N:24][CH:23]=[C:20]3[S:21][CH:22]=2)[N:12]([C:10]([O:9][CH2:6][CH:7]=[CH2:8])=[O:11])[CH2:13]1)(=[O:4])[CH3:2]

Komponenten

6

Edukt 2

HCID 23670855Potassium ethanethioateHCID 86756315(3R,5S)-1-allyloxycarbonyl-5-[1-hydroxy-(imidazo[5,1-b]thiazol-3-yl)methyl]-3-methanesulfonyloxypyrrolidine

Produkt 1

HCID 86756316(3S,5S)-3-Acetylthio-1-allyloxycarbonyl-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-3-yl)methyl]pyrrolidineAusbeute 72,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Potassium thioacetate (134 mg) is added to a solution of 314 mg of (3R,5S)-1-allyloxycarbonyl-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-3-yl)methyl]-3-methanesulfonyloxypyrrolidine (stereoisomer A) in a mixture of 4 ml of dry DMF and 2 ml of dry toluene, and the mixture is stirred in an argon atmosphere at a bath temperature of 70° C. for 22 hr. The mixture is diluted with 60 ml of ethyl acetate and washed twice with semi-saturated saline, and the organic layer is dried over magnesium sulfate and filtered. The solvent is removed by evaporation under reduced pressure, and the residue is dried under reduced pressure by means of a vacuum pump. The dark red oil is purified by flash column chromatography on silica gel (ethyl acetate) to give 217 mg of the title compound as a slightly red amorphous material.

Aufarbeitung

  1. washwashed twice with semi-saturated saline
  2. dry with materialthe organic layer is dried over magnesium sulfate
  3. filtrationfiltered
  4. customThe solvent is removed by evaporation under reduced pressure
  5. customthe residue is dried under reduced pressure by means of a vacuum pump
  6. customThe dark red oil is purified by flash column chromatography on silica gel (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-70c402430e374d75a6466e5f07f64ece
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06180622B2

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