Sodium Chloride → methyl (2S,4S)-4-acetylthio-1-methyl-2-pyrrolidinecarboxylate

HRID 9943

Reaktionsgleichung

Reaktionsgleichung von HRID 9943
[C:1]([O-:4])(=[S:3])[CH3:2].[K+].CS(O[C@H:11]1[CH2:15][N:14]([CH3:16])[C@H:13]([C:17]([O:19][CH3:20])=[O:18])[CH2:12]1)(=O)=O.C(OCC)(=O)C.[Cl-].[Na+]>C(O)C.O>[C:1]([S:3][C@@H:11]1[CH2:15][N:14]([CH3:16])[C@H:13]([C:17]([O:19][CH3:20])=[O:18])[CH2:12]1)(=[O:4])[CH3:2]

Komponenten

6

Edukt 4

HCID 5234Sodium ChlorideHCID 8857Ethyl AcetateHCID 12082503Methyl (2S,4R)-4-methylsulfonyloxy-1-methyl-2-pyrrolidinecarboxylateHCID 23670855Potassium ethanethioate

Produkt 1

HCID 12082502methyl (2S,4S)-4-acetylthio-1-methyl-2-pyrrolidinecarboxylateAusbeute 97,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 19096565Water ethanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Potassium thioacetate (677 mg) was added to a solution of methyl (2S,4R)-4-methylsulfonyloxy-1-methyl-2-pyrrolidinecarboxylate (609 mg) obtained from Reference example 4 in ethanol/water (9:1) (6 ml), and the resulting mixture was stirred at 80° C. for 3 hours, and then the mixture was allowed to stand overnight at the same temperature. Ethyl acetate (20 mL) and 10% aqueous sodium chloride solution (10 mL) were added to the reaction mixture, which was then extracted. The organic layer was separated from the aqueous layer, which was washed with water (10 mL). The solvent of the organic layer was removed by distillation under reduced pressure to give the title compound (543 mg, yield 97%).

Aufarbeitung

  1. waitto stand overnight at the same temperature
  2. extractionwas then extracted
  3. customThe organic layer was separated from the aqueous layer, which
  4. washwas washed with water (10 mL)
  5. customThe solvent of the organic layer was removed by distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c3fa110c818b49349c5d166723b662c8
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091363B2

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