Hydrochloric Acid → (1R,5S,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-[[(Z)-2-(4-(N-4-nitrobenzyloxycarbonyl-L-valyloxymethyl)thiazol-5-yl)ethen-1-yl]thio]-1-carbapen-2-em-3-carboxylic acid

HRID 1799735ノート

反応式

HRID 1799735 の反応式
[OH:1][C@@H:2]([C@H:4]1[C:47](=[O:48])[N:6]2[C:7]([C:41]([O:43]CC=C)=[O:42])=[C:8]([S:11]/[CH:12]=[CH:13]\[C:14]3[S:18][CH:17]=[N:16][C:15]=3[CH2:19][O:20][C:21](=[O:40])[C@H:22]([CH:37]([CH3:39])[CH3:38])[NH:23][C:24]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=3)=[O:25])[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].CC1(C)CC(=O)CC(=O)C1.C(OCC)(=O)C.Cl>O1CCCC1.[Cl-].[Na+].O>[OH:1][C@@H:2]([C@H:4]1[C:47](=[O:48])[N:6]2[C:7]([C:41]([OH:43])=[O:42])=[C:8]([S:11]/[CH:12]=[CH:13]\[C:14]3[S:18][CH:17]=[N:16][C:15]=3[CH2:19][O:20][C:21](=[O:40])[C@H:22]([CH:37]([CH3:39])[CH3:38])[NH:23][C:24]([O:26][CH2:27][C:28]3[CH:29]=[CH:30][C:31]([N+:34]([O-:36])=[O:35])=[CH:32][CH:33]=3)=[O:25])[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 31358DimedoneHCID 131728009Allyl (1R,5S,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-[[(Z)-2-(4-(N-4-nitrobenzyloxycarbonyl-L-valinyloxy-methyl)thiazol-5-yl)ethen-1-yl]thio]-1-carbapen-2-em-3-carboxylate

生成物 1

HCID 131728010(1R,5S,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-[[(Z)-2-(4-(N-4-nitrobenzyloxycarbonyl-L-valyloxymethyl)thiazol-5-yl)ethen-1-yl]thio]-1-carbapen-2-em-3-carboxylic acid収率 67.2%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

Allyl (1R,5S,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-[[(Z)-2-(4-(N-4-nitrobenzyloxycarbonyl-L-valinyloxy-methyl)thiazol-5-yl)ethen-1-yl]thio]-1-carbapen-2-em-3-carboxylate (500 mg) and 250 mg of dimedone were dissolved in 10 ml of tetrahydrofuran. Tetrakistriphenylphosphine palladium (82 mg) was added to the solution, and the mixture was stirred under an argon atmosphere at room temperature for 30 min. The reaction mixture was poured into 50 ml of 20% brine and 50 ml of ethyl acetate, and the mixture was adjusted to pH 0.6 by the addition of a 1 N aqueous hydrochloric acid solution, followed by separation. The organic layer was dried over anhydrous magnesium sulfate, and the solid was removed by filtration, and the solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography on Sephadex LH-20 (dichloromethane:methanol=1:1) to give 317 mg of (1R,5S,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-[[(Z)-2-(4-(N-4-nitrobenzyloxycarbonyl-L-valyloxymethyl)thiazol-5-yl)ethen-1-yl]thio]-1-carbapen-2-em-3-carboxylic acid.

後処理

  1. customfollowed by separation
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solid was removed by filtration
  4. customthe solvent was removed by distillation under the reduced pressure
  5. customThe residue was purified by column chromatography on Sephadex

出典と根拠

ORDレコード
ord-18fbf70288504569885dfb9920ba3010
出典データセット
uspto-grants-2013_01
特許番号
US08344154B2

反応ノート

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