Ethyl Acetate → HCID 23387866、化合物

HRID 1839347

反応式

HRID 1839347 の反応式
[OH:1][C@@H:2]([C@H:4]1[C:24](=[O:25])[N:6]2[C:7]([C:21]([O-:23])=[O:22])=[C:8]([C:11]3[S:15][C:14]4=[C:16]([S:19][CH3:20])[N:17]=[CH:18][N:13]4[CH:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].[Na+].[CH3:27][O:28][C:29]1[CH:39]=[CH:38][CH:37]=[CH:36][C:30]=1[C:31]([O:33][CH2:34]Cl)=[O:32].[C:40](OCC)(=O)C>CN(C=O)C.[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[OH:1][C@@H:2]([C@H:4]1[C:24](=[O:25])[N:6]2[C:7]([C:21]([O:23][CH:34]([O:33][C:31](=[O:32])[C:30]3[CH:36]=[CH:37][CH:38]=[CH:39][C:29]=3[O:28][CH3:27])[CH3:40])=[O:22])=[C:8]([C:11]3[S:15][C:14]4=[C:16]([S:19][CH3:20])[N:17]=[CH:18][N:13]4[CH:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 234492712-Methoxybenzoyloxymethyl chlorideHCID 23669370Sodium (1s,5r,6s)-6-((1r)-1-hydroxyethyl)-1-methyl-2-(7-methylthio-imidazo[5,1-b]thiazol-2-yl)-1-carbapen-2-em-3-carboxylate

生成物 1

HCID 23387866HCID 23387866、化合物

試薬・触媒・溶媒 2

HCID 66133Benzyl triethylammonium chloride触媒HCID 6228Dimethylformamide溶媒

実験手順

Sodium (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-(7-methylthioimidazo[5,1-b]thiazol2-yl)-1-carbapen-2-em-3-carboxylate (170 mg) was dissolved in 2 ml of DMF. Triethylbenzylammonium chloride (193 mg) and 182 mg of 2-methoxybenzoyloxymethyl chloride were added to the solution in an argon atmosphere. The mixture was stirred under ice cooling for 2 hr and then stirred at room temperature for 5 hr. Ethyl acetate (30 ml) was added to the reaction solution. The mixture was washed twice with 20 ml of semisaturated brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then concentrated to a volume of 5 ml under the reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane: methanol=40: 1) to give 131 mg of the title compound.

後処理

  1. stirringstirred at room temperature for 5 hr
  2. washThe mixture was washed twice with 20 ml of semisaturated brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to a volume of 5 ml under the reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (dichloromethane: methanol=40: 1)

出典と根拠

ORDレコード
ord-969dd61671a94d4e94269ab287b6d977
出典データセット
uspto-grants-2004_01
特許番号
US06677331B2

関連ノート

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