Sodium Hydroxide → HCID 14305079, Verbindung

HRID 37280

Reaktionsgleichung

Reaktionsgleichung von HRID 37280
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C@@H:6]1[CH2:10][C@@H:9]([OH:11])[CH2:8][N:7]1[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1)=[O:13].[N+:25]([C:28]1[CH:38]=[CH:37][C:31]([CH2:32][O:33][C:34](Cl)=[O:35])=[CH:30][CH:29]=1)([O-:27])=[O:26].[OH-].[Na+]>O.O1CCCC1>[OH:11][C@H:9]1[CH2:8][N:7]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)=[O:13])[C@H:6]([C:2]2[N:1]([C:34]([O:33][CH2:32][C:31]3[CH:30]=[CH:29][C:28]([N+:25]([O-:27])=[O:26])=[CH:38][CH:37]=3)=[O:35])[CH:5]=[CH:4][N:3]=2)[CH2:10]1

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 782054-Nitrobenzyl chloroformateHCID 14305085HCID 14305085, Verbindung

Produkt 1

HCID 14305079HCID 14305079, VerbindungAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of (2S,4R)-2-(imidazol-2-yl)-4-hydroxy-1- (4-nitrobenzyloxycarbonyl)pyrrolidine (1.0 g) in a mixture of water (10 ml) and tetrahydrofuran (20 ml) was dropwise added a solution of 4-nitrobenzyloxycarbonyl chloride (0.85 g) in tetrahydrofuran (5 ml) under ice-cooling with stirring, keeping the pH between 9 and 10 with 4N aqueous sodium hydroxide. The mixture was stirred under the same condition for 1 hour, extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated to give (2S, 4R)-4-hydroxy-2-[N-(4-nitrobenzyloxycarbonyl) imidazol-2-yl]-1-(4-nitrobenzyloxycarbonyl) pyrrolidine (970 mg).

Aufarbeitung

  1. temperaturecooling
  2. stirringThe mixture was stirred under the same condition for 1 hour
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-019b77393650477bac61c52cfdb87446
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05420122

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