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

HRID 362083노트

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HRID 362083 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f5c87a1cfec240a4a76f4ed62416eeb1
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05866564

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