Methane → HCID 131715368, compound

HRID 256453Notes

Reaction equation

HRID 256453 reaction equation
Cl.C([NH:4][C:5]1[S:6][C:7]([Br:31])=[C:8]([C:10](=[N:28][O:29][CH3:30])[C:11]([NH:13][CH:14]2[C:26](=[O:27])[N:16]3[C:17]([C:23]([OH:25])=[O:24])=[CH:18][CH:19]([O:21][CH3:22])[S:20][C@H:15]23)=[O:12])[N:9]=1)=O.C.[OH-].[Na+]>CO.O>[NH2:4][C:5]1[S:6][C:7]([Br:31])=[C:8]([C:10](=[N:28][O:29][CH3:30])[C:11]([NH:13][CH:14]2[C:26](=[O:27])[N:16]3[C:17]([C:23]([OH:25])=[O:24])=[CH:18][CH:19]([O:21][CH3:22])[S:20][C@H:15]23)=[O:12])[N:9]=1

Participants

7

Reactant 4

HCID 297MethaneHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131715367HCID 131715367, compound

Product 1

HCID 131715368HCID 131715368, compoundYield 90.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

Conc. hydrochloric acid (0.7 ml.) was added to a solution of 7-[2-(2-formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-2-methoxy-3-cephem-4-carboxylic acid (syn isomer, 1.4 g.) in methanol (45 ml.) and stirred at room temperature for 2 hrs. and further for 3.5 hrs. under ice-cooling. The reaction mixture was treated with activated charcoal. Water (30 ml.) was added to the solution and adjusted to pH 6.5 with 1N-aqueous sodium hydroxide, and methanol was distilled off. Ethyl acetate was added to the residue and adjusted to pH 2.5 with 1N-hydrochloric acid. The ethyl acetate layer was separated and the aqueous layer was washed with ethyl acetate. The ethyl acetate solution obtained above and the washings were combined, dried over magnesium sulfate, treated with activated charcoal and evaporated in vacuo. The residue was pulverized with diethyl ether, and the precipitates were collected by filtration and dried to give 7-[2-(2-amino-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-2-methoxy-3 -cephem-4-carboxylic acid (syn isomer, 1.2 g.).

Workup

  1. waitand further for 3.5 hrs
  2. temperatureunder ice-cooling
  3. distillationwas distilled off
  4. additionEthyl acetate was added to the residue
  5. customThe ethyl acetate layer was separated
  6. washthe aqueous layer was washed with ethyl acetate
  7. customThe ethyl acetate solution obtained above and the washings
  8. dry with materialdried over magnesium sulfate
  9. additiontreated with activated charcoal
  10. customevaporated in vacuo
  11. filtrationthe precipitates were collected by filtration
  12. customdried

Sources & evidence

ORD record
ord-9e4912d547864b91b04ffee284353e09
Source dataset
uspto-grants-1987_10
Patent number
US04703046

Reaction notes

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