Methane → HCID 21530757, 화합물

HRID 893901노트

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HRID 893901 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

HCID 21530757HCID 21530757, 화합물

시약·촉매·용매 1

HCID 241Benzene용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bcebb83e2d734f59af87b00df28194d9
출처 데이터셋
uspto-grants-1981_08
특허 번호
US04282145

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