Methane → HCID 21530757、化合物

HRID 893901ノート

反応式

HRID 893901 の反応式
C(N1C(=O)CCC1=O)(=O)C.C[Si](C)(C)N1C(=O)CCC1=O.C[Si](C)(C)[O:24][C:25]([CH:27]([N:31]1[CH:34]([S:35][N:36]2[C:40](=[O:41])[CH2:39][CH2:38][C:37]2=[O:42])[CH:33]([NH:43][C:44](=[O:52])[CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:32]1=[O:53])[C:28]([CH3:30])=[CH2:29])=[O:26].C>C1C=CC=CC=1>[C:25]([CH:27]([N:31]1[CH:34]([S:35][N:36]2[C:37](=[O:42])[CH2:38][CH2:39][C:40]2=[O:41])[CH:33]([NH:43][C:44](=[O:52])[CH2:45][C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:32]1=[O:53])[C:28]([CH3:30])=[CH2:29])([OH:26])=[O:24]

参加物

6

反応物 4

HCID 297MethaneHCID 11457741N-acetylsuccinimideHCID 116654792,5-Pyrrolidinedione, 1-(trimethylsilyl)-HCID 86733530HCID 86733530、化合物

生成物 1

HCID 21530757HCID 21530757、化合物

試薬・触媒・溶媒 1

HCID 241Benzene溶媒2 回

実験手順

A mixture of 5.3 g of benzylpenicillin-S-sulphoxide, 50 g of N-acetylsuccinimide, 12.5 ml of N-trimethylsilylsuccinimide and 35 ml of benzene was refluxed for 16 hours. The reaction mixture (containing 1-(1-trimethylsilyloxycarbonyl-2-methylprop-2-enyl)-3-phenylacetamido-4-succinimidothio-azetidin-2-one) was then allowed to cool to room temperature, diluted with benzene (200 ml), treated with decolourizing charcoal, and evaporated to dryness. The residue was purified by column chromatography on silica gel using 5% acetic acid in ethyl acetate as eluent. The fractions containing the major component of the original residue were combined, evaporated to dryness and the residue triturated with diethyl ether. The precipitate was chromatographed a second time to obtain 1-(1-carboxy-2-methylprop-2-enyl)-3-phenylacetamido-4-succinimidothioazetidin-2-one in a pure state. The structure was confirmed by PMR and IR spectroscopy.

後処理

  1. temperaturewas refluxed for 16 hours
  2. customevaporated to dryness
  3. customThe residue was purified by column chromatography on silica gel using 5% acetic acid in ethyl acetate as eluent
  4. additionThe fractions containing the major component of the original residue
  5. customevaporated to dryness
  6. customthe residue triturated with diethyl ether
  7. customThe precipitate was chromatographed a second time

出典と根拠

ORDレコード
ord-bcebb83e2d734f59af87b00df28194d9
出典データセット
uspto-grants-1981_08
特許番号
US04282145

反応ノート

読み込み中…