Formaldehyde → HCID 15280796, compound

HRID 257998Notes

Reaction equation

HRID 257998 reaction equation
[Br:1][C@H:2]1[C:28](=[O:29])[N:4]2[C:5]([C:12]([O:14][CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])=[C:6]([CH3:11])[CH2:7][S:8](=[O:10])(=[O:9])[C@H:3]12.Cl.[CH3:31]NC.C=O.C(O)(C)(C)C>C(Cl)Cl>[Br:1][C@H:2]1[C:28](=[O:29])[N:4]2[C:5]([C:12]([O:14][CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[O:13])=[C:6]([CH3:11])[C:7](=[CH2:31])[S:8](=[O:9])(=[O:10])[C@H:3]12

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 6386tert-ButanolHCID 10473Dimethylamine, hydrochlorideHCID 15280795HCID 15280795, compound

Product 1

HCID 15280796HCID 15280796, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
95 °C

Procedure

To a stirred solution of benzhydryl 7α-bromo-3-methyl-3-cephem-4-carboxylate-1,1-dioxide (2.8 g, 0.0059 mol) in methylene chloride (12 ml) were added dimethylamine hydrochloride (1.44 g, 0.0176 mol), formaldehyde (0.61 g, 0.020 mol) and t-butyl alcohol (100 ml), the mixture was heated to reflux at 95° C. for 3 hours. Solvent was removed under reduced pressure and the residue was dissolved in methylene chloride, washed with water, dried over sodium sulfate and concentrated to dryness. The residue was purified by column chromatography with a solvent gradient of 10 to 25% ethyl acetate/hexane to afford benzhydryl 7α-bromo-2-methylene-3-methyl-3-cephem-4-carboxylate-1, 1-dioxide (2.0 g, 69.5%) as a white foam. IR (Nujol) ν max 1720, 1800 cm-1.

Workup

  1. temperaturethe mixture was heated
  2. customSolvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in methylene chloride
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by column chromatography with a solvent gradient of 10 to 25% ethyl acetate/hexane

Sources & evidence

ORD record
ord-69699a4ffe8942ebaf3caac961085745
Source dataset
uspto-grants-1993_11
Patent number
US05264429

Reaction notes

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