Bromotrimethylsilane → HCID 131712385, compound

HRID 2231427Notes

Reaction equation

HRID 2231427 reaction equation
C[Si](C([Si](C)(C)C)C(N)=O)(C)C.C[Si](Br)(C)C.[P:18]([CH2:22][CH2:23][O:24][N:25]=[C:26]([C:53]1[N:54]=[C:55]([NH:58]C=O)[S:56][CH:57]=1)[C:27]([NH:29][CH:30]1[C:51](=[O:52])[N:32]2[C:33]([C:48]([OH:50])=[O:49])=[C:34]([CH2:37][S:38][C:39]3[S:40][C:41]4[CH:47]=[CH:46][CH:45]=[CH:44][C:42]=4[N:43]=3)[CH2:35][S:36][C@H:31]12)=[O:28])([OH:21])([OH:20])=[O:19]>C(Cl)Cl>[P:18]([CH2:22][CH2:23][O:24][N:25]=[C:26]([C:53]1[N:54]=[C:55]([NH2:58])[S:56][CH:57]=1)[C:27]([NH:29][CH:30]1[C:51](=[O:52])[N:32]2[C:33]([C:48]([OH:50])=[O:49])=[C:34]([CH2:37][S:38][C:39]3[S:40][C:41]4[CH:47]=[CH:46][CH:45]=[CH:44][C:42]=4[N:43]=3)[CH2:35][S:36][C@H:31]12)=[O:28])([OH:21])([OH:20])=[O:19]

Participants

5

Reactant 3

HCID 76113BromotrimethylsilaneHCID 11708267BistrimethylsilylacetamidHCID 131712386HCID 131712386, compound

Product 1

HCID 131712385HCID 131712385, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 7-[2-{2-(O,O-diethylphosphono)ethoxyimino}-2-(2-formamidothiazol-4-yl)acetamido]-3-(2-benzothiazolyl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (2.59 g.), methylene chloride (30 ml.) and bis(trimethylsilyl)acetamide (2.14 g.) was stirred for 30 minutes at 18° to 20° C. and thereto was added trimethylsilyl bromide (2.68 g.) followed by stirring for 5 hours and 45 minutes at 19° to 21° C. The reaction mixture containing 7-[2-(2-phosphonoethoxyimino)-2-(2-formamidothiazol-4-yl)acetamido]-3-(2-benzothiazolyl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) was concentrated and to the residue were added methanol (30 ml.) and conc. hydrochloric acid (3 ml.). The mixture was stirred for 1.5 hours at room temperature and then evaporated. The residue was dissolved in an aqueous solution of sodium bicarbonate and the solution was washed with ethyl acetate and then adjusted to pH about 2 with 10% hydrochloric acid. The precipitates were collected by filtration under cooling, washing with water, dried under reduced pressure and then suspended in methanol (20 ml.). After conc. hydrochloric acid was added to the suspension to dissolve the precipitates, the resulting solution was treated with activated charcoal and then thereto was added dropwise a mixture of conc. ammonia water and methanol (1:5) whereby the pH was adjusted to 3 to 4. The precipitates were collected by filtration under cooling to give a powder of the title compound (0.85 g.), mp. 170° to 210° C.

Workup

  1. stirringby stirring for 5 hours and 45 minutes at 19° to 21° C
  2. concentrationwas concentrated and to the residue
  3. additionwere added methanol (30 ml.) and conc. hydrochloric acid (3 ml.)
  4. stirringThe mixture was stirred for 1.5 hours at room temperature
  5. customevaporated
  6. dissolutionThe residue was dissolved in an aqueous solution of sodium bicarbonate
  7. washthe solution was washed with ethyl acetate
  8. filtrationThe precipitates were collected by filtration
  9. temperatureunder cooling
  10. washwashing with water
  11. customdried under reduced pressure
  12. additionAfter conc. hydrochloric acid was added to the suspension
  13. dissolutionto dissolve the precipitates
  14. additionthe resulting solution was treated with activated charcoal
  15. additionwas added dropwise
  16. additiona mixture of conc. ammonia water and methanol (1:5) whereby the pH
  17. filtrationThe precipitates were collected by filtration
  18. temperatureunder cooling

Sources & evidence

ORD record
ord-85de34cb2dfb4daea1f88afca2aea9f0
Source dataset
uspto-grants-1988_11
Patent number
US04782158

Reaction notes

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