Hypodiphosphorous tetraiodide → 1,1-Dimethylethyl 7-[2-(2-tritylaminothiazol-4-yl)-2-methoxyimino-acetamido]-8-oxo-3-methoxymethyl-4-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylate

HRID 1770192Notes

Reaction equation

HRID 1770192 reaction equation
P(I)(I)P(I)I.[C:7]([NH:26][C:27]1[S:28][CH:29]=[C:30]([C:32](=[N:56][O:57][CH3:58])[C:33]([NH:35][CH:36]2[C:43](=[O:44])[N:42]3[CH:37]2[CH2:38][S:39][CH:40]([CH2:53][O:54][CH3:55])[C:41]3(O)[C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])=[O:34])[N:31]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>N1C=CC=CC=1>[C:7]([NH:26][C:27]1[S:28][CH:29]=[C:30]([C:32](=[N:56][O:57][CH3:58])[C:33]([NH:35][CH:36]2[C:43](=[O:44])[N:42]3[CH:37]2[CH2:38][S:39][C:40]([CH2:53][O:54][CH3:55])=[C:41]3[C:45]([O:47][C:48]([CH3:49])([CH3:50])[CH3:51])=[O:46])=[O:34])[N:31]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 83484Hypodiphosphorous tetraiodideHCID 539719981,1-Dimethylethyl 7-[2-(2-tritylaminothiazol-4-yl)-2-methoxyimino-acetamido]-8-oxo-2-hydroxy-3-methoxymethyl-4-thia-1-azabicyclo[4,2,0]octane-2-carboxylate

Product 1

HCID 545215821,1-Dimethylethyl 7-[2-(2-tritylaminothiazol-4-yl)-2-methoxyimino-acetamido]-8-oxo-3-methoxymethyl-4-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylateYield 23.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4.44 g of diphosphorus tetraiodide were suspended in 35 ml of pyridine, and after stirring for 5 minutes, 3.058 g of 1,1-dimethylethyl 7-[2-(2-tritylaminothiazol-4-yl)-2-methoxyimino-acetamido]-8-oxo-2-hydroxy-3-methoxymethyl-4-thia-1-azabicyclo[4,2,0]octane-2-carboxylate were added all at once with stirring for 2 hours 40 minutes. The pyridine was distilled off and the residue was taken up in 50 ml of ethyl acetate. After filtering, 50 ml of N hydrochloric acid were added to the filtrate with vigorous stirring and the decanted organic phase was washed with water, dried and concentrated to dryness under reduced pressure. The residue was chromatographed over silica and eluted with a mixture of methylene chloride and ethyl acetate (85-15). The fractions of interest were concentrated to dryness and crystallized from methanol to obtain 703 mg of 1,1-dimethylethyl 7-[2-(2-tritylaminothiazol-4-yl)-2-methoxyimino-acetamido]-8-oxo-3-methoxymethyl-4-thia-1-azabicyclo[4,2,0]oct-2-en-2-carboxylate

Workup

  1. stirringwith stirring for 2 hours 40 minutes
  2. distillationThe pyridine was distilled off
  3. filtrationAfter filtering
  4. addition50 ml of N hydrochloric acid were added to the filtrate
  5. stirringwith vigorous stirring
  6. washthe decanted organic phase was washed with water
  7. customdried
  8. concentrationconcentrated to dryness under reduced pressure
  9. customThe residue was chromatographed over silica
  10. washeluted with a mixture of methylene chloride and ethyl acetate (85-15)
  11. concentrationThe fractions of interest were concentrated to dryness
  12. customcrystallized from methanol

Sources & evidence

ORD record
ord-d0693cb6a7fd4b7d95b67cf9640024e5
Source dataset
uspto-grants-1995_01
Patent number
US05385897

Reaction notes

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