Triethylamine → (2S,4S)-4-Mercapto-2-{4-[2-(p-nitrobenzyloxycarbonyl)oxyethyl]-1-piperazinylcarbonyl}-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

HRID 362087Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 362087
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=O)=O.O[C@H]1[CH2:18][N:17]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)=[O:20])[C@H:16]([C:32]([N:34]2[CH2:39][CH2:38][N:37]([CH2:40][CH2:41][O:42][C:43]([O:45][CH2:46][C:47]3[CH:52]=[CH:51][C:50]([N+:53]([O-:55])=[O:54])=[CH:49][CH:48]=3)=[O:44])[CH2:36][CH2:35]2)=[O:33])[CH2:15]1>O1CCCC1>[SH:9][C@@H:8]1[CH2:18][N:17]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)=[O:20])[C@H:16]([C:32]([N:34]2[CH2:35][CH2:36][N:37]([CH2:40][CH2:41][O:42][C:43]([O:45][CH2:46][C:47]3[CH:48]=[CH:49][C:50]([N+:53]([O-:55])=[O:54])=[CH:51][CH:52]=3)=[O:44])[CH2:38][CH2:39]2)=[O:33])[CH2:15]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22881632(2S,4R)-4-hydroxy-2-{4-[2-(4-nitrobenzyloxycarbonyl)oxyethyl]-1-piperazinyl carbonyl}-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Produkt 1

HCID 15814079(2S,4S)-4-Mercapto-2-{4-[2-(p-nitrobenzyloxycarbonyl)oxyethyl]-1-piperazinylcarbonyl}-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

89 μl of triethylamine and 50 μl of methanesulfonyl chloride were added, whilst ice-cooling, to a solution of 321 mg of (2S,4R)-4-hydroxy-2-{4-[2-(4-nitrobenzyloxycarbonyl)oxyethyl]-1-piperazinylcarbonyl}-1-(4-nitrobenzyloxycarbonyl)pyrrolidine in 3.2 ml of dry tetrahydrofuran, and the resulting mixture was stirred at between 0° C. and 5° C. for 30 minutes and then at room temperature for a further 1 hour. At the end of tis time, the reaction mixture was concentrated by evaporation under reduced pressure, and the resulting residue was mixed with an aqueous solution of sodium hydrogencarbonate; the mixture was then extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, to give 345 mg of the title compound as a powder.

Aufarbeitung

  1. waitat room temperature for a further 1 hour
  2. concentrationAt the end of tis time, the reaction mixture was concentrated by evaporation under reduced pressure
  3. additionthe resulting residue was mixed with an aqueous solution of sodium hydrogencarbonate
  4. extractionthe mixture was then extracted with ethyl acetate
  5. washThe extract was washed with an aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0645b58c54b34ee494ecf6d9368e833c
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05866564

Notizen zur Reaktion

Wird geladen…