Hydrochloric Acid → Hydrochloric Acid

HRID 1708509Notes

Reaction equation

HRID 1708509 reaction equation
N[C@@H:2]1[C:9](=[O:10])[N:8]2[C@@H:3]1[S:4][CH2:5][C:6](N1N=NC(C)=N1)=[C:7]2[C:11]([OH:13])=[O:12].N12CCCN=C1CCCCC2.[C:31]([O:37]CI)(=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33].[ClH:40]>CC(C)=O.C(OCCCC)(=O)C.C(O)(C)C>[ClH:40].[C:31]([OH:37])(=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33].[O:10]=[C:9]1[N:8]2[CH:3]([S:4][CH2:5][CH:6]=[C:7]2[C:11]([OH:13])=[O:12])[CH2:2]1.[ClH:40]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 104401Iodomethyl pivalateHCID 18655884HCID 18655884, compound

Product 2

HCID 313Hydrochloric AcidHCID 131718753HCID 131718753, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 3776IsopropanolSolventHCID 31272Butyl AcetateSolvent2×

Procedure

12.15 g of (6R,7R)-7-amino-3-(5-methyl-2H-tetrazol-2-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene- 2-carboxylic acid are suspended in 60 ml of acetone. The suspension is treated within 15 minutes at 20°-25° while stirring with 6.3 g of 1.8-diazabicyclo[5.4.0]undec-7-ene (DBU), 10.6 g of pivaloyloxymethyl iodide are added to the resulting solution at 15° and the mixture is stirred for 15 minutes without cooling. 250 ml of n-butyl acetate are now added thereto. Crystallized-out DBU hydroiodide is filtered off under suction and washed with 50 ml of n-butyl acetate. The yellow filtrate is washed twice with 125 ml of saturated sodium chloride solution each time and filtered through a fluted filter. 100 ml of solvent are distilled off in a water-jet vacuum at 35°. The solution is again filtered and treated while stirring with 8.4 g of p-toluenesulphonic acid . H2O. The crystallized-out material is filtered off under suction after stirring for 30 minutes and washed with n-butyl acetate. The material obtained is suspended in 200 ml of n-butyl acetate and treated while stirring with 20 ml of 5.2N hydrochloric acid in isopropanol, whereby a solution results. This solution is stirred for 1 hour, whereby crystallization occurs. The crystallized-out hydrochloride is filtered off under suction, washed with n-butyl acetate and n-hexane and dried overnight in a water-jet vacuum at 35°. There are obtained 13.9 g (77.75%) of methylene (6R,7R)-7-amino-3-[5-methyl-2H-tetrazol-2-yl)methyl]-8-oxo-5-thia-1azabicyclo[4.2.0]oct-2-ene-2-carboxylate pivalate hydrochloride as white crystals (C16H22N6O5S. HCl; MW: 446.91).

Workup

  1. additionThe suspension is treated within 15 minutes at 20°-25°
  2. additionare added to the resulting solution at 15°
  3. temperaturewithout cooling
  4. filtrationCrystallized-out DBU hydroiodide is filtered off under suction
  5. washwashed with 50 ml of n-butyl acetate
  6. washThe yellow filtrate is washed twice with 125 ml of saturated sodium chloride solution each time
  7. filtrationfiltered through
  8. filtrationa fluted filter
  9. distillation100 ml of solvent are distilled off in a water-jet vacuum at 35°
  10. filtrationThe solution is again filtered
  11. additiontreated
  12. stirringwhile stirring with 8.4 g of p-toluenesulphonic acid
  13. filtrationThe crystallized-out material is filtered off under suction
  14. stirringafter stirring for 30 minutes
  15. washwashed with n-butyl acetate
  16. customThe material obtained
  17. additiontreated
  18. customresults
  19. stirringThis solution is stirred for 1 hour
  20. customwhereby crystallization
  21. filtrationThe crystallized-out hydrochloride is filtered off under suction
  22. washwashed with n-butyl acetate and n-hexane
  23. dry with materialdried overnight in a water-jet vacuum at 35°

Sources & evidence

ORD record
ord-69931111110743cab525934b9ad5eee8
Source dataset
uspto-grants-1994_10
Patent number
US05359057

Reaction notes

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