Formaldehyde → HCID 67658279, compound

HRID 258001Notes

Reaction equation

HRID 258001 reaction equation
[Br:1][C@H:2]1[C:19](=[O:20])[N:4]2[C:5]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[C:6]([CH3:11])[CH2:7][S:8](=[O:10])(=[O:9])[C@H:3]12.Cl.[CH3:22]NC.C(Cl)Cl.C=O>C(O)(C)(C)C>[Br:1][C@H:2]1[C:19](=[O:20])[N:4]2[C:5]([C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])=[C:6]([CH3:11])[C:7](=[CH2:22])[S:8](=[O:9])(=[O:10])[C@H:3]12

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 6344DichloromethaneHCID 10473Dimethylamine, hydrochlorideHCID 67657400HCID 67657400, compound

Product 1

HCID 67658279HCID 67658279, compoundYield 5.6%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of t-butyl 7α-bromo-3-methyl-3-cephem -4-carboxylate 1,1-dioxide (700 mg, 1.9 mmol), dimethylamine hydrochloride (460 mg, 5.7 mmol), methylene chloride (3 ml) and t-butyl alcohol (50 ml), formaldehyde (0.57 g, 37% w/v) was heated to reflux at 80°-90° C. for 20 hours. t-Butyl alcohol was removed under reduced pressure and the residue was dissolved in methylene chloride, washed with water, brine, dried and concentrated to give 200 mg of crude product which was purified over silica column using methylene chloride as eluant to give 40 mg of pure t-butyl 7α-bromo-2-methylene-3-methyl-3-cephem-4-carboxylate 1,1-dioxide.

Workup

  1. temperaturewas heated
  2. temperatureto reflux at 80°-90° C. for 20 hours
  3. customt-Butyl alcohol was removed under reduced pressure
  4. dissolutionthe residue was dissolved in methylene chloride
  5. washwashed with water, brine
  6. customdried
  7. concentrationconcentrated
  8. customto give 200 mg of crude product which
  9. customwas purified over silica column

Sources & evidence

ORD record
ord-1d812d9e7d0440fcb680da2e92c818d1
Source dataset
uspto-grants-1993_11
Patent number
US05264429

Reaction notes

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