Water → Methyl 7-benzamido-3-bromomethyl-3-cephem-4-carboxylate-1-oxide

HRID 1902907Notes

Reaction equation

HRID 1902907 reaction equation
[Br:1]N1C(=O)CCC1=O.[C:9]([NH:17][CH:18]1[C:31](=[O:32])[N:20]2[C:21]([C:27]([O:29][CH3:30])=[O:28])=[C:22]([CH3:26])[CH2:23][S:24](=[O:25])[C@H:19]12)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O>ClCCl.C(O)(=O)C.[W]>[C:9]([NH:17][CH:18]1[C:31](=[O:32])[N:20]2[C:21]([C:27]([O:29][CH3:30])=[O:28])=[C:22]([CH2:26][Br:1])[CH2:23][S:24](=[O:25])[C@H:19]12)(=[O:16])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

7

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 70500625Methyl 7-benzamido-3-methyl-3-cephem-4-carboxylate-1-oxide

Product 1

HCID 70500589Methyl 7-benzamido-3-bromomethyl-3-cephem-4-carboxylate-1-oxideYield 58.8%

Reagents, catalysts & solvents 3

HCID 23964TungstenCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

1.2 g (6.8 mmoles) of N-bromosuccinimide were added to an ice-cooled solution of 1.4 g (4 mmoles) of methyl 7-benzamido-3-methyl-3-cephem-4-carboxylate-1-oxide in a mixture of 25 ml of dichloromethane and 50 ml of acetic acid. The mixture was stirred and irradiated with a 150 W tungsten lamp for 1.5 hours. The reaction mixture was poured into water and dichloromethane and the organic layer was separated and washed three times with 500 ml of water. After treatment with activated charcoal, it was dried over magnesium sulfate and filtered. The filtrate was concentrated to about 20 ml in vacuo and the product was precipiated by addition of 150 ml of diethyl ether. The mixture was filtered and the product was washed with diethyl ether. It was crystallized by dissolving it in 100 ml of refluxing dichloromethane and precipitation by addition of 100 ml of diethyl ether to obtain 1.0 g pure methyl 7-benzamido-3-bromomethyl-3-cephem-4-carboxylate-1-oxide (yield 58.8%).

Workup

  1. customthe organic layer was separated
  2. washwashed three times with 500 ml of water
  3. dry with materialAfter treatment with activated charcoal, it was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated to about 20 ml in vacuo
  6. additionthe product was precipiated by addition of 150 ml of diethyl ether
  7. filtrationThe mixture was filtered
  8. washthe product was washed with diethyl ether
  9. customIt was crystallized
  10. dissolutionby dissolving it in 100 ml of refluxing dichloromethane
  11. customprecipitation
  12. additionby addition of 100 ml of diethyl ether

Sources & evidence

ORD record
ord-b43c7e4f6f454dc49a98ed8d709fb256
Source dataset
uspto-grants-1982_12
Patent number
US04366315

Reaction notes

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