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 1376826Notes

Reaction equation

HRID 1376826 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 suspended in 35 ml of pyridine was stirred for 5 minutes and then 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 and the mixture was stirred for 2 hours 40 minutes. The pyridine was distilled off and the residue was taken up in 50 ml of ethyl acetate. The mixture was filtered, and 50 ml of N hydrochloric acid were added to the liltrate which was vigorously stirred. The organic phase was decanted, washed with water, dried and concentrated to dryness under reduced pressure. The residue was chromatographed on silica with a methylene chloride-ethyl acetate mixture (85-15) and the recovered fractions 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-ene-2-carboxylate.

Workup

  1. stirringwas stirred for 2 hours 40 minutes
  2. distillationThe pyridine was distilled off
  3. filtrationThe mixture was filtered
  4. addition50 ml of N hydrochloric acid were added to the liltrate which
  5. stirringwas vigorously stirred
  6. customThe organic phase was decanted
  7. washwashed with water
  8. customdried
  9. concentrationconcentrated to dryness under reduced pressure
  10. customThe residue was chromatographed on silica with a methylene chloride-ethyl acetate mixture (85-15)
  11. concentrationthe recovered fractions were concentrated to dryness
  12. customcrystallized from methanol

Sources & evidence

ORD record
ord-625530ad22b445f680300cfb610923c1
Source dataset
uspto-grants-1997_09
Patent number
US05663164

Reaction notes

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