Water → HCID 23387834、化合物

HRID 989885

反応式

HRID 989885 の反応式
[CH3:1][C:2]([CH3:13])([O:6][C:7]([O:9][CH:10](Cl)[CH3:11])=[O:8])[CH2:3][CH2:4][CH3:5].[OH:14][C@@H:15]([C@H:17]1[C:37](=[O:38])[N:19]2[C:20]([C:34]([O-:36])=[O:35])=[C:21]([C:24]3[S:28][C:27]4=[C:29]([S:32][CH3:33])[N:30]=[CH:31][N:26]4[CH:25]=3)[C@H:22]([CH3:23])[C@H:18]12)[CH3:16].[Na+].O>CN(C=O)C.[Ag]I>[OH:14][C@@H:15]([C@H:17]1[C:37](=[O:38])[N:19]2[C:20]([C:34]([O:36][CH:10]([O:9][C:7]([O:6][C:2]([CH3:13])([CH3:1])[CH2:3][CH2:4][CH3:5])=[O:8])[CH3:11])=[O:35])=[C:21]([C:24]3[S:28][C:27]4=[C:29]([S:32][CH3:33])[N:30]=[CH:31][N:26]4[CH:25]=3)[C@H:22]([CH3:23])[C@H:18]12)[CH3:16]

参加物

6

反応物 3

HCID 962WaterHCID 234491371-(1,1-Dimethyl-1-butyloxycarbonyloxy)ethyl 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 23387834HCID 23387834、化合物収率 29.9%

試薬・触媒・溶媒 2

HCID 24563Silver iodide触媒HCID 6228Dimethylformamide溶媒3 回

実験手順

A solution of 156.6 mg of 1-(1,1-dimethyl-1-butyloxycarbonyloxy)ethyl chloride in 2.0 ml of DMF was added to a suspension of 176.1 mg of silver iodide in 2.0 ml of DMF. The mixture was stirred in an argon atmosphere at room temperature for one hr. A solution of 200.0 mg of sodium(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 in 1.0 ml of DMF was added thereto, followed by stirring for 3 hr. Water (10 ml) was added to the reaction solution to terminate the reaction. The system was extracted three times with 10 ml of ethyl acetate, followed by washing three times with 30 ml of semisaturated brine. The organic layer was dried over anhydrous magnesium sulfate and filtered. The residue was purified by chromatography on silica gel (chloroform:methanol=20:1) to give 82.3 mg of the title compound.

後処理

  1. stirringby stirring for 3 hr
  2. customto terminate
  3. customthe reaction
  4. extractionThe system was extracted three times with 10 ml of ethyl acetate
  5. washby washing three times with 30 ml of semisaturated brine
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe residue was purified by chromatography on silica gel (chloroform:methanol=20:1)

出典と根拠

ORDレコード
ord-675901b43e19495ab0dd9350190c3749
出典データセット
uspto-grants-2002_10
特許番号
US06458780B1

関連ノート

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