benzhydryl (2S,3R,5R)-3-formyl-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate → Benzhydryl (E)-(2S,3S,5R)-3-methyl-3-[2-(1,2,4-oxadiazol-3-yl)-vinyl]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

HRID 1683170Notes

Reaction equation

HRID 1683170 reaction equation
[CH:1]([C@:3]1([CH3:27])[S:9][C@H:8]2[N:5]([C:6](=[O:10])[CH2:7]2)[C@H:4]1[C:11]([O:13][CH:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=O.[Cl-].[O:29]1[CH:33]=[N:32][C:31]([CH2:34][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[N:30]1>C1OC1CC>[CH3:27][C@@:3]1(/[CH:1]=[CH:34]/[C:31]2[N:32]=[CH:33][O:29][N:30]=2)[S:9][C@H:8]2[N:5]([C:6](=[O:10])[CH2:7]2)[C@H:4]1[C:11]([O:13][CH:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:12]

Participants

4

Reactant 2

HCID 10762402benzhydryl (2S,3R,5R)-3-formyl-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateHCID 19038908(1,2,4-Oxadiazol-3-yl)methyl-triphenylphosphonium chloride

Product 1

HCID 86750939Benzhydryl (E)-(2S,3S,5R)-3-methyl-3-[2-(1,2,4-oxadiazol-3-yl)-vinyl]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

Reagents, catalysts & solvents 1

HCID 78341,2-EpoxybutaneSolvent

Procedure

1.14 g (3.0 mmol) of benzhydryl (2S,3R,5R)-3-formyl-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate were dissolved in 15 ml of 1,2-butylene oxide, treated with 1.38 g (3.6 mmol) of (1,2,4-oxadiazol-3-yl)methyl-triphenylphosphonium chloride and refluxed for 10 hours. Subsequently, the mixture was filtered, the filtrate is evaporated and the residual brown oil was chromatographed over silica gel (0.040-0.063 mm particle size) with methylene chloride as the eluent.

Workup

  1. temperaturerefluxed for 10 hours
  2. filtrationSubsequently, the mixture was filtered
  3. customthe filtrate is evaporated
  4. customthe residual brown oil was chromatographed over silica gel (0.040-0.063 mm particle size) with methylene chloride as the eluent

Sources & evidence

ORD record
ord-c4a65ff1737a4902b976254ae253a971
Source dataset
uspto-grants-1997_06
Patent number
US05637579

Reaction notes

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