Water → p-Nitrobenzyl 3-Methyl-2-(2-chlorosulfinyl-4-oxo-3-phenoxyacetamido-1-azetidinyl)-3-butenoate

HRID 261314Notes

Reaction equation

HRID 261314 reaction equation
O.[O:2]([CH2:9][C:10]([NH:12][CH:13]1[C:35](=[O:36])[N:15]2[CH:16]([C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=3)=[O:23])[C:17]([CH3:21])([CH3:20])[S:18](=[O:19])[C@H:14]12)=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:37]N1C(=O)C2=CC=CC=C2C1=O>C1(C)C=CC=CC=1>[CH3:20][C:17](=[CH2:21])[CH:16]([N:15]1[C:35](=[O:36])[CH:13]([NH:12][C:10](=[O:11])[CH2:9][O:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH:14]1[S:18]([Cl:37])=[O:19])[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=1)=[O:23]

Participants

5

Reactant 3

HCID 962WaterHCID 18997N-ChlorophthalimideHCID 67928276p-Nitrobenzyl 6-phenoxyacetamido-2,2-dimethylpenam-3-carboxylate-1-oxide

Product 1

HCID 9936995p-Nitrobenzyl 3-Methyl-2-(2-chlorosulfinyl-4-oxo-3-phenoxyacetamido-1-azetidinyl)-3-butenoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Tolune (425 ml.) was heated in equipment containing a Dean-Stark water trap to azeotropically remove any moisture which may be present, and 25 ml. of toluene were removed thereby. To the remaining toluene were added 10.0 g. (20 mmol.) of p-nitrobenzyl 6-phenoxyacetamido-2,2-dimethylpenam-3-carboxylate-1-oxide, the toluene being maintained at a temperature slightly below reflux. Toluene (200 ml.) was separately distilled, and 4.0 g. (22 mmol.) of N-chlorophthalimide were added. The resulting solution (warm) was added dropwise to the solution of the penicillin sulfoxide ester over a period of 30 minutes. The mixture remained a light yellow solution throughout addition. The mixture then was refluxed for 55 minutes after which time a sample was removed, and nmr (CDCl3) analysis of the sample indicated virtually entire conversion of the penicillin sulfoxide ester to the title compound.

Workup

  1. temperatureTolune (425 ml.) was heated in equipment
  2. customto azeotropically remove any moisture which
  3. customof toluene were removed
  4. additionTo the remaining toluene were added 10.0 g
  5. temperaturebelow reflux
  6. distillationToluene (200 ml.) was separately distilled
  7. temperatureThe resulting solution (warm)
  8. additionthroughout addition
  9. temperatureThe mixture then was refluxed for 55 minutes after which time a sample
  10. customwas removed

Sources & evidence

ORD record
ord-b09265afed434271a6d671f92183fc25
Source dataset
uspto-grants-1979_08
Patent number
US04165315

Reaction notes

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