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

HRID 362083Notes

Reaction equation

HRID 362083 reaction equation
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

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 11020280o-Nitrobenzyl chloroformateHCID 15282196(2S,4S)-2-[4-(2-hydroxyethyl)piperazinylcarbonyl]-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f5c87a1cfec240a4a76f4ed62416eeb1
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

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