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

HRID 1679572Notes

Reaction equation

HRID 1679572 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 1140TolueneSolvent2×

Procedure

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

Sources & evidence

ORD record
ord-9ac5dc081e674a428cea35f2b0a87473
Source dataset
uspto-grants-1978_03
Patent number
US04081440

Reaction notes

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