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

HRID 362084Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 362084
C(=O)([O-])O.[Na+].FC(F)(F)S(O)(=O)=O.FC(F)(F)S(O)(=O)=O.[SH:22][C@@H:23]1[CH2:27][N:26]([C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=2)=[O:29])[C@H:25]([C:41]([N:43]2[CH2:48][CH2:47][N:46]([CH2:49][CH2:50][O:51][C:52]([O:54][CH2:55][C:56]3[CH:61]=[CH:60][C:59]([N+:62]([O-:64])=[O:63])=[CH:58][CH:57]=3)=[O:53])[CH2:45][CH2:44]2)=[O:42])[CH2:24]1>>[SH:22][C@@H:23]1[CH2:27][N:26]([C:28]([O:30][CH2:31][C:32]2[CH:33]=[CH:34][C:35]([N+:38]([O-:40])=[O:39])=[CH:36][CH:37]=2)=[O:29])[C@H:25]([C:41]([N:43]2[CH2:44][CH2:45][N:46]([CH2:49][CH2:50][O:51][C:52]([O:54][CH2:55][C:56]3[CH:57]=[CH:58][C:59]([N+:62]([O-:64])=[O:63])=[CH:60][CH:61]=3)=[O:53])[CH2:47][CH2:48]2)=[O:42])[CH2:24]1

Komponenten

3

Edukt 2

HCID 516892Sodium BicarbonateHCID 86747844(2S,4S)-4-Mercapto-2-{4-[2-(4-nitrobenzyloxycarbonyl)oxyethyl]-1-piperazinylcarbonyl}-1-(4-nitrobenzyloxycarbonyl)pyrrolidine bis(trifluoromethanesulfonate)

Produkt 1

HCID 15814079(2S,4S)-4-Mercapto-2-{4-[2-(p-nitrobenzyloxycarbonyl)oxyethyl]-1-piperazinylcarbonyl}-1-(p-nitrobenzyloxycarbonyl)pyrrolidineAusbeute 88,6 %

Versuchsvorschrift

20 ml of a 5% w/v aqueous solution of sodium hydrogencarbonate was added to 862 mg of (2S,4S)-4-mercapto-2-{4-[2-(4-nitrobenzyloxycarbonyl)oxyethyl]-1-piperazinylcarbonyl}-1-(4-nitrobenzyloxycarbonyl)pyrrolidine bis(trifluoromethanesulfonate), and the mixture was extracted with 50 ml of ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 20:1 by volume mixture of ethyl acetate and methanol as the eluent, to afford 514 mg of the title compound, as a powder.

Aufarbeitung

  1. extractionthe mixture was extracted with 50 ml of ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customthe resulting residue was purified by column chromatography through silica gel
  6. additionby volume mixture of ethyl acetate and methanol as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-0c1a5195b6df45c1ac1fd55750300910
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05866564

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