4-Nitrobenzyl chloroformate → (2S,4S)-2-{4-[2-(4-Nitrobenzyloxycarbonyl)oxyethyl]-1-piperazinylcarbonyl}-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 37341

反応式

HRID 37341 の反応式
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)=[O:3].[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][CH2:32][C:33]3[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=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>CN(C)C1C=CN=CC=1.C(Cl)Cl.C(OCC)(=O)C>[N+:12]([C:9]1[CH:10]=[CH:11][C:6]([CH2:5][O:4][C:2]([O:15][CH2:16][CH2:17][N:18]2[CH2:19][CH2:20][N:21]([C:24]([C@@H:26]3[CH2:30][C@H:29]([S:31][CH2:32][C:33]4[CH:34]=[CH:35][C:36]([O:39][CH3:40])=[CH:37][CH:38]=4)[CH2:28][N:27]3[C:41]([O:43][CH2:44][C:45]3[CH:50]=[CH:49][C:48]([N+:51]([O-:53])=[O:52])=[CH:47][CH:46]=3)=[O:42])=[O:25])[CH2:22][CH2:23]2)=[O:3])=[CH:7][CH:8]=1)([O-:14])=[O:13]

参加物

6

反応物 2

HCID 782054-Nitrobenzyl chloroformateHCID 15282196(2S,4S)-2-[4-(2-hydroxyethyl)piperazinylcarbonyl]-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

生成物 1

HCID 57120790(2S,4S)-2-{4-[2-(4-Nitrobenzyloxycarbonyl)oxyethyl]-1-piperazinylcarbonyl}-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine収率 89.3%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

5.86 g of 4-dimethylaminopyridine and a solution of 10.35 g of p-nitrobenzyl chloroformate in 40 ml of anhydrous methylene chloride were added to a solution of 22.35 g of (2S,4S)-2-[4-(2-hydroxyethyl)-1-piperazinylcarbonyl]-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (prepared as described in Preparation 7) in 160 ml of anhydrous methylene chloride, and the resulting mixture was stirred at room temperature for 1 hour. At the end of this time, the reaction mixture was diluted with 300 ml of ethyl acetate and washed with 100 ml of water, with 100 ml of a saturated aqueous solution of sodium hydrogencarbonate and with 100 ml of a saturated aqueous solution of sodium chloride, in that order. The solvents were removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel. Those fractions eluted with ethyl acetate were collected and concentrated by evaporation under reduced pressure, to give 26.35 g of the title compound as a colorless powder.

後処理

  1. washwashed with 100 ml of water, with 100 ml of a saturated aqueous solution of sodium hydrogencarbonate and with 100 ml of a saturated aqueous solution of sodium chloride, in that order
  2. customThe solvents were removed by distillation under reduced pressure
  3. customthe resulting residue was purified by column chromatography through silica gel
  4. washThose fractions eluted with ethyl acetate
  5. customwere collected
  6. concentrationconcentrated by evaporation under reduced pressure

出典と根拠

ORDレコード
ord-9aa44092c3d043ec9d68913f3aec6e7f
出典データセット
uspto-grants-1995_05
特許番号
US05420119

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