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Racemic 1,1-dimethylethyl 7-[2-(2-tritylaminothiazol-4-yl)-2-methoxyimino-acetamido]-3-(ethoxycarbonylmethylthio)-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylate → Racemic 7-[2-(2-aminothiazol-4-yl)-2-methoxyimino-acetamido]-3-(ethoxycarbonylmethylthio)-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylic acid

HRID 1376841
ノート
印刷プレビュー

反応式

HRID 1376841 の反応式
C([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:53][O:54][CH3:55])[C:27]([NH:29][CH:30]2[C:37](=[O:38])[N:36]3[CH:31]2[CH2:32][S:33][C:34]([S:46][CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49])=[C:35]3[C:39]([O:41]C(C)(C)C)=[O:40])=[O:28])[N:25]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(O)=O>[NH2:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:53][O:54][CH3:55])[C:27]([NH:29][CH:30]2[C:37](=[O:38])[N:36]3[CH:31]2[CH2:32][S:33][C:34]([S:46][CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49])=[C:35]3[C:39]([OH:41])=[O:40])=[O:28])[N:25]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

3

反応物 1

HCID 53798384Racemic 1,1-dimethylethyl 7-[2-(2-tritylaminothiazol-4-yl)-2-methoxyimino-acetamido]-3-(ethoxycarbonylmethylthio)-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylate

生成物 1

HCID 54438830Racemic 7-[2-(2-aminothiazol-4-yl)-2-methoxyimino-acetamido]-3-(ethoxycarbonylmethylthio)-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylic acid収率 55.8%

試薬・触媒・溶媒 1

HCID 284Formic Acid溶媒

反応条件

温度
50 °C

実験手順

A mixture of 200 mg of the product of Step B dissolved in 4 ml of 66% formic acid was stirred at 50° C. for 2 hours, after which the solution was cooled and filtered. The filtrate was concentrated to dryness under reduced pressure and the residue was re-dissolved in ethanol. The solvent was evaporated and 20 ml of ether were added with stirring for 30 minutes. Then, the crude products was separated and chromatographed on silica and eluted with a mixture of methylene chloride and methanol (8-2). After crystallization from ether, 70 mg of racemic 7-[2-(2-aminothiazol-4-yl)-2-methoxyimino-acetamido]-3-(ethoxycarbonylmethylthio)-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylic acid melting at >210° C. (decomposes) were obtained.

後処理

  1. temperatureafter which the solution was cooled
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated to dryness under reduced pressure
  4. dissolutionthe residue was re-dissolved in ethanol
  5. customThe solvent was evaporated
  6. addition20 ml of ether were added
  7. stirringwith stirring for 30 minutes
  8. customThen, the crude products was separated
  9. customchromatographed on silica
  10. washeluted with a mixture of methylene chloride and methanol (8-2)
  11. customAfter crystallization from ether

出典と根拠

ORDレコード
ord-ae9747bf9d2f4c4c9a2c836262cf18d8
出典データセット
uspto-grants-1997_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05663164

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート