Trichloroacetyl isocyanate → (2S,4S)-2-[4-(2-carbamoyloxyethyl)-1-piperazinylcarbonyl]-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 37340

反応式

HRID 37340 の反応式
ClC(Cl)(Cl)[C:3]([N:5]=C=O)=[O:4].[OH:10][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][N:16]([C:19]([C@@H:21]2[CH2:25][C@H:24]([S:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)[CH2:23][N:22]2[C:36]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][C:43]([N+:46]([O-:48])=[O:47])=[CH:42][CH:41]=2)=[O:37])=[O:20])[CH2:15][CH2:14]1>C(Cl)Cl>[C:3]([O:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][N:16]([C:19]([C@@H:21]2[CH2:25][C@H:24]([S:26][CH2:27][C:28]3[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=3)[CH2:23][N:22]2[C:36]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][C:43]([N+:46]([O-:48])=[O:47])=[CH:42][CH:41]=2)=[O:37])=[O:20])[CH2:17][CH2:18]1)(=[O:4])[NH2:5]

参加物

4

反応物 2

HCID 76400Trichloroacetyl isocyanateHCID 15282196(2S,4S)-2-[4-(2-hydroxyethyl)piperazinylcarbonyl]-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

生成物 1

HCID 57049434(2S,4S)-2-[4-(2-carbamoyloxyethyl)-1-piperazinylcarbonyl]-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

1.43 ml of trichloroacetyl isocyanate was added, whilst ice-cooling, to a solution of 5.59 g of (2S,4S)-2-[4-(2-hydroxyethyl)-1-piperazinylcarbonyl]-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine in 50 ml of anhydrous methylene chloride, and the resulting mixture was stirred at the same temperature for 30 minutes. At the end of this time, the solvent was removed by distillation under reduced pressure, the resulting residue was dissolved in 120 ml of methanol, and the solution was stirred at room temperature for 4.5 hours in the presence of 35 g of silica gel (a product of Merck & Co., Inc., silica gel 60, 230-400 mesh). The silica gel was removed by filtration, and the filtrate was freed from methanol by evaporation under reduced pressure. The resulting residue was purified by column chromatography through silica gel. Those fractions eluted with an 8:1 by volume mixture of ethyl acetate and methanol were collected and concentrated by evaporation under reduced pressure, to give 5.76 g of the title compound as a colorless powder.

後処理

  1. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  2. dissolutionthe resulting residue was dissolved in 120 ml of methanol
  3. stirringthe solution was stirred at room temperature for 4.5 hours in the presence of 35 g of silica gel (a product of Merck & Co
  4. customThe silica gel was removed by filtration
  5. customthe filtrate was freed from methanol by evaporation under reduced pressure
  6. customThe resulting residue was purified by column chromatography through silica gel
  7. washThose fractions eluted with an 8:1 by volume mixture of ethyl acetate and methanol
  8. customwere collected
  9. concentrationconcentrated by evaporation under reduced pressure

出典と根拠

ORDレコード
ord-eb6967dad5e34faf99513df095eec382
出典データセット
uspto-grants-1995_05
特許番号
US05420119

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