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

HRID 362083Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 362083
ClC(O[CH2:5][C:6]1C=C[CH:9]=[CH:8][C:7]=1[N+:12]([O-:14])=[O:13])=O.[OH:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][N:21]([C:24]([C@@H:26]2[CH2:30][C@H:29]([S:31]CC3C=CC(OC)=CC=3)[CH2:28][N:27]2[C:41]([O:43][CH2:44][C:45]2[CH:50]=[CH:49][C:48]([N+:51]([O-:53])=[O:52])=[CH:47][CH:46]=2)=[O:42])=[O:25])[CH2:20][CH2:19]1.[C:54]([O:57][CH2:58][CH3:59])(=[O:56])C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[SH:31][C@@H:29]1[CH2:28][N:27]([C:41]([O:43][CH2:44][C:45]2[CH:46]=[CH:47][C:48]([N+:51]([O-:53])=[O:52])=[CH:49][CH:50]=2)=[O:42])[C@H:26]([C:24]([N:21]2[CH2:22][CH2:23][N:18]([CH2:17][CH2:16][O:15][C:54]([O:57][CH2:58][C:59]3[CH:9]=[CH:8][C:7]([N+:12]([O-:14])=[O:13])=[CH:6][CH:5]=3)=[O:56])[CH2:19][CH2:20]2)=[O:25])[CH2:30]1

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 11020280o-Nitrobenzyl chloroformateHCID 15282196(2S,4S)-2-[4-(2-hydroxyethyl)piperazinylcarbonyl]-4-(4-methoxybenzylthio)-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 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 5.86 g of 4-dimethylaminopyridine and 10.35 g of o-nitrobenzyl chloroformate in 40 ml of dry methylene chloride was added, whilst ice-cooling, to a solution of 22.35 g of (2S,4S)-2-[4-(2-hydroxyethyl)-1-piperazinylcarbonyl]-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine in 160 ml of dry methylene chloride, and the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was then diluted with 300 ml of ethyl acetate and the dilute solution was washed, in turn, with water (100 ml, once), with an aqueous solution of sodium hydrogencarbonate (100 ml, once) and with an aqueous solution of sodium chloride (100 ml, once). The solvent was then removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through slica gel, using ethyl acetate as the eluent, to give 26.35 g of the title compound, as a colorless powder.

Aufarbeitung

  1. washthe dilute solution was washed, in turn, with water (100 ml
  2. customThe solvent was then removed by distillation under reduced pressure
  3. customthe resulting residue was purified by column chromatography through slica gel

Quellen und Nachweise

ORD-Eintrag
ord-f5c87a1cfec240a4a76f4ed62416eeb1
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05866564

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