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

HRID 362089ノート

反応式

HRID 362089 の反応式
ClC(O[CH2:5][C:6]1C=C[CH:9]=[CH:8][C:7]=1[N+:12]([O-:14])=[O:13])=O.C([S:18][C@@H:19]1[CH2:23][N:22]([C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=2)=[O:25])[C@H:21]([C:37]([N:39]2[CH2:44][CH2:43][N:42]([CH2:45][CH2:46][OH:47])[CH2:41][CH2:40]2)=[O:38])[CH2:20]1)(=O)C.[C:48]([O:51][CH2:52][CH3:53])(=[O:50])C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[SH:18][C@@H:19]1[CH2:23][N:22]([C:24]([O:26][CH2:27][C:28]2[CH:29]=[CH:30][C:31]([N+:34]([O-:36])=[O:35])=[CH:32][CH:33]=2)=[O:25])[C@H:21]([C:37]([N:39]2[CH2:44][CH2:43][N:42]([CH2:45][CH2:46][O:47][C:48]([O:51][CH2:52][C:53]3[CH:9]=[CH:8][C:7]([N+:12]([O-:14])=[O:13])=[CH:6][CH:5]=3)=[O:50])[CH2:41][CH2:40]2)=[O:38])[CH2:20]1

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 11020280o-Nitrobenzyl chloroformateHCID 86752004(2S,4S)-4-acetylthio-2-[4-(2-hydroxyethyl)-1-piperazinylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 1.10 g of o-nitrobenzyl chloroformate in 10 ml of methylene chloride was added, whilst ice-cooling, to a solution of 1.63 g of (2S,4S)-4-acetylthio-2-[4-(2-hydroxyethyl)-1-piperazinylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine and 0.62 g of 4-dimethylaminopyridine in 15 ml of methylene chloride and the resulting mixture was stirred at the same temperature for 2 hours. At the end of this time, the reaction mixture was diluted with 100 ml of ethyl acetate, and the dilute solution was washed, in turn, with 100 ml of an aqueous solution of sodium hydrogencarbonate, with 100 ml of water and with 100 ml of an aqueous solution of sodium chloride. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through slica gel, using a gradient elution method, with mixtures of ethyl acetate and methanol ranging from 30:1 to 25:1 by volume as the eluent to give 1.86 g of the title compound, as a powder. The infrared absorption spectrum and nuclear magnetic resonance spectrum of the compound thus obtained were identical with those of the compound prepared as described in step 90(b)(ii) above.

後処理

  1. washthe dilute solution was washed, in turn, with 100 ml of an aqueous solution of sodium hydrogencarbonate, with 100 ml of water and with 100 ml of an aqueous solution of sodium chloride
  2. customThe solvent was removed by distillation under reduced pressure
  3. customthe resulting residue was purified by column chromatography through slica gel
  4. washa gradient elution method

出典と根拠

ORDレコード
ord-8c759623b83840fb9c01bad663cace62
出典データセット
uspto-grants-1999_02
特許番号
US05866564

反応ノート

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