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4-nitrobenzyl (1R, 5S, 6S)-2-[(2S, 4S)-2-[4-(N-4-nitrobenzyloxycarbonylacetimidoyl)piperazin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate → (1R, 5S, 6S)-2-[(2S, 4S)-2-(4-Acetimidoylpiperazin-1-ylcarbonyl)pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylic acid

HRID 727594
ノート
印刷プレビュー

反応式

HRID 727594 の反応式
[N+](C1C=CC(COC([N:12]=[C:13]([N:15]2[CH2:20][CH2:19][N:18]([C:21]([C@@H:23]3[CH2:27][C@H:26]([S:28][C:29]4[C@H:30]([CH3:53])[C@@H:31]5[C@@H:48]([C@H:49]([OH:51])[CH3:50])[C:47](=[O:52])[N:32]5[C:33]=4[C:34]([O:36]CC4C=CC([N+]([O-])=O)=CC=4)=[O:35])[CH2:25][N:24]3C(OCC3C=CC([N+]([O-])=O)=CC=3)=O)=[O:22])[CH2:17][CH2:16]2)[CH3:14])=O)=CC=1)([O-])=O>O1CCCC1.O>[C:13]([N:15]1[CH2:16][CH2:17][N:18]([C:21]([C@@H:23]2[CH2:27][C@H:26]([S:28][C:29]3[C@H:30]([CH3:53])[C@@H:31]4[C@@H:48]([C@H:49]([OH:51])[CH3:50])[C:47](=[O:52])[N:32]4[C:33]=3[C:34]([OH:36])=[O:35])[CH2:25][NH:24]2)=[O:22])[CH2:19][CH2:20]1)(=[NH:12])[CH3:14]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 1

HCID 1317204064-nitrobenzyl (1R, 5S, 6S)-2-[(2S, 4S)-2-[4-(N-4-nitrobenzyloxycarbonylacetimidoyl)piperazin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

生成物 1

HCID 9956142(1R, 5S, 6S)-2-[(2S, 4S)-2-(4-Acetimidoylpiperazin-1-ylcarbonyl)pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylic acid収率 38%

試薬・触媒・溶媒 2

HCID 962Water
溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

5.10 g of 4-nitrobenzyl (1R, 5S, 6S)-2-{(2S, 4S)-2-[4-(N-4-nitrobenzyloxycarbonylacetimidoyl)piperazin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-ylthio}-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate [prepared as described in step (a) above] were dissolved in 100 ml of a 6:4 by volume mixture of tetrahydrofuran and water, and the mixture was hydrogenated by bubbling hydrogen through it at room temperature for 2.5 hours in the presence of 5.0 g of 10% w/w palladium-on-charcoal. The catalyst was filtered off, and the filtrate was washed with diethyl ether and then concentrated by evaporation under reduced pressure. The resulting residue was purified by reverse phase column chromatography through 250 ml of Cosmo Sil 75C18 -PREP (a trade mark for a product of Nacalai Tesque), using water, 5% v/v aqueous acetonitrile and 7% v/v aqueous acetonitrile, in that order, as the eluent. Those fractions containing the title compound were combined, concentrated by evaporation under reduced pressure and lyophilized to give 940 mg of the title compound, as a powder.

後処理

  1. customby bubbling hydrogen through it at room temperature for 2.5 hours in the presence of 5.0 g of 10% w/w palladium-on-charcoal
  2. filtrationThe catalyst was filtered off
  3. washthe filtrate was washed with diethyl ether
  4. concentrationconcentrated by evaporation under reduced pressure
  5. customThe resulting residue was purified by reverse phase column chromatography through 250 ml of Cosmo Sil 75C18 -PREP (a trade mark for a product of Nacalai Tesque),
  6. additionThose fractions containing the title compound
  7. concentrationconcentrated by evaporation under reduced pressure

出典と根拠

ORDレコード
ord-4a16577d411e4cd89b4714b6a41fbbcd
出典データセット
uspto-grants-1998_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05712267

反応ノート

読み込み中…

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