Formaldehyde → HCID 67856236, compound

HRID 257996Notes

Reaction equation

HRID 257996 reaction equation
[Cl: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>[Cl: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 67657505HCID 67657505, compound

Product 1

HCID 67856236HCID 67856236, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
95 °C

Procedure

Benzhydryl 7α-chloro-3-methyl-3-cephem-4-carboxylate 1,1-dioxide (9.3 g, 0.0215 mol) was dissolved in methylene chloride (35 ml), dimethylamine hydrochloride (4.9 g, 0.0645 mol), formaldehyde solution (2.25 g, 0.075 mol) and t-butyl alcohol (300 ml) were added and the mixture was heated to reflux at 95° C. for 4 hours. After removing the solvent under reduced pressure the residue was redissolved in methylene chloride, washed successively with water, dried over sodium sulfate and concentrated. The product was purified over a silica column using hexane-ethyl acetate mixture as the eluant to yield benzhydryl 7α-chloro-2-methylene-3-methyl-3-cephem-4-carboxylate 1,1-dioxide (3.6 g, 40%) as a white foam. IR (Nujol) ν max 1723, 1800 cm-1.

Workup

  1. temperaturethe mixture was heated
  2. customAfter removing the solvent under reduced pressure the residue
  3. dissolutionwas redissolved in methylene chloride
  4. washwashed successively with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe product was purified over a silica column

Sources & evidence

ORD record
ord-4f62484adcd74af8acf8298fe277ad93
Source dataset
uspto-grants-1993_11
Patent number
US05264429

Reaction notes

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