Sodium Hydroxide → (2S,4R)-4-methanesulfonyloxy-2-(4-methylthiosemicarbazidocarbonyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 37258

Reaktionsgleichung

Reaktionsgleichung von HRID 37258
P(Cl)(Cl)(Cl)=O.[C:6]([C@@H:9]1[CH2:13][C@@H:12]([O:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH2:11][N:10]1[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1)=[O:20])(O)=[O:7].[CH3:32][NH:33][C:34](=[S:37])[NH:35][NH2:36].[OH-].[Na+]>O1CCCC1.O.CN(C)C=O>[CH3:18][S:15]([O:14][C@H:12]1[CH2:11][N:10]([C:19]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][C:26]([N+:29]([O-:31])=[O:30])=[CH:27][CH:28]=2)=[O:20])[C@H:9]([C:6]([NH:36][NH:35][C:34]([NH:33][CH3:32])=[S:37])=[O:7])[CH2:13]1)(=[O:17])=[O:16]

Komponenten

8

Edukt 4

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 2723853N-MethylhydrazinecarbothioamideHCID 13502650trans-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)-L-proline

Produkt 1

HCID 14305077(2S,4R)-4-methanesulfonyloxy-2-(4-methylthiosemicarbazidocarbonyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidineAusbeute 81,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

To a mixture of dimethylformamide (2.9 ml) and tetrahydrofuran (6 ml) was dropwise added phosphorus oxychloride (2.8 ml) at -5°∫5° C. and the mixture was stirred at the same temperature for 30 minutes. To the mixture was added a solution of (2S,4R)-2- carboxy-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (9.65 g) in tetrahydrofuran (20 ml) at -5°∫5° C., followed by stirring at the same temperature for 30 minutes. The mixture was dropwise added to a solution of 4-methylthiosemicarbazide (25 g) in a mixture of water (200 ml) and tetrahydrofuran (200 ml) at 0°-10° C. with stirring, keeping the pH between 8-9 with 1N aqueous sodium hydroxide. The mixture was stirred at the same condition for 2 hours. Tetrahydrofuran was evaporated under reduced pressure to give precipitates. The precipitates were collected by filtration, washed with water and diisopropyl ether successively, and dried over phosphorus pentoxide to give (2S, 4R)-4-methanesulfonyloxy -2-(4-methylthiosemicarbazidocarbonyl)-1-(4-nitrobenzyloxycarbonyl) pyrrolidine (9.61 g).

Aufarbeitung

  1. customat -5°
  2. custom∫5° C.
  3. stirringby stirring at the same temperature for 30 minutes
  4. stirringwith stirring
  5. stirringThe mixture was stirred at the same condition for 2 hours
  6. customTetrahydrofuran was evaporated under reduced pressure
  7. customto give
  8. customprecipitates
  9. filtrationThe precipitates were collected by filtration
  10. washwashed with water and diisopropyl ether successively
  11. dry with materialdried over phosphorus pentoxide

Quellen und Nachweise

ORD-Eintrag
ord-0c8c3713669a4ab5982b2d36c3469622
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05420122

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