Formaldehyde → HCID 67657566, compound

HRID 257810Notes

Reaction equation

HRID 257810 reaction equation
[Cl:1][C@H:2]1[C:23](=[O:24])[N:4]2[C:5]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[C:6]([CH2:11][O:12][C:13](=[O:15])[CH3:14])[CH2:7][S:8](=[O:10])(=[O:9])[C@H:3]12.[CH2:25](Cl)Cl.Cl.CNC.C=O>C(O)(C)(C)C>[Cl:1][C@H:2]1[C:23](=[O:24])[N:4]2[C:5]([C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])=[C:6]([CH2:11][O:12][C:13](=[O:15])[CH3:14])[C:7](=[CH2:25])[S:8](=[O:9])(=[O:10])[C@H:3]12

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 6344DichloromethaneHCID 10473Dimethylamine, hydrochlorideHCID 125700tert-Butyl 3-[(acetyloxy)methyl]-7-chloro-5,5,8-trioxo-5lambda~6~-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Product 1

HCID 67657566HCID 67657566, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of t-butyl 7α-chloro-3-acetoxymethyl-3-cephem-4-carboxylate-1,1-dioxide (1.9 g), methylene chloride (3 ml), dimethylamine hydrochloride (0.817 g), t-butanol (80 ml) and formaldehyde solution (I.10 ml, 37% w/v in water) was heated to reflux at 90° C. for 3 hours. Solvent was removed under reduced pressure and the residue was dissolved in methylene chloride, washed with water, brine, dried and concentrated to give 1.6 g (81.6%) of t-butyl 7α-chloro-2-methylene-3-acetoxymethyl-3-cephem-4-carboxylate-1,1-dioxide, m.p. 148°-149° C. This product without further purification was used in the next step.

Workup

  1. temperaturewas heated
  2. customSolvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in methylene chloride
  4. washwashed with water, brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6d88c87393c74a90a97ba49a5fa29a96
Source dataset
uspto-grants-1993_11
Patent number
US05264430

Reaction notes

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