Methane → HCID 21530757, compound

HRID 893901Notes

Reaction equation

HRID 893901 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

HCID 21530757HCID 21530757, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bcebb83e2d734f59af87b00df28194d9
Source dataset
uspto-grants-1981_08
Patent number
US04282145

Reaction notes

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