Ethyl chloroformate → HCID 131711444, compound

HRID 126756Notes

Reaction equation

HRID 126756 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[OH:7][N:8]=[C:9]([C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([OH:39])[CH:34]=1)[C:10]([NH:12][CH:13]1[C:31](=[O:32])[N:15]2[C:16]([C:28]([O-:30])=[O:29])=[C:17]([CH2:20][S:21][C:22]3[N:26]([CH3:27])[N:25]=[N:24][N:23]=3)[CH2:18][S:19][C@H:14]12)=[O:11].[Na+]>O.N1C=CC=CC=1>[CH2:5]([O:4][C:2]([O:7][N:8]=[C:9]([C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([OH:39])[CH:34]=1)[C:10]([NH:12][CH:13]1[C:31](=[O:32])[N:15]2[C:16]([C:28]([OH:30])=[O:29])=[C:17]([CH2:20][S:21][C:22]3[N:26]([CH3:27])[N:25]=[N:24][N:23]=3)[CH2:18][S:19][C@H:14]12)=[O:11])=[O:3])[CH3:6]

Participants

5

Reactant 2

HCID 10928Ethyl chloroformateHCID 131711445HCID 131711445, compound

Product 1

HCID 131711444HCID 131711444, compoundYield 52.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1049PyridineSolvent

Procedure

Ethyl chloroformate (10.9 g.) was dropwise added by small portions with stirring and ice-cooling to a solution of sodium 7-[2-hydroxyimino-2-(3-hydroxyphenyl)acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylate (syn isomer) (16.3 g.) in a mixture of water (80 ml.) and pyridine (80 ml.), and the mixture was stirred for 1 hour at the same temperature. Water (200 ml.) was added thereto and the mixture was washed with ether. The aqueous layer was adjusted to pH 2 with hydrochloric acid and extracted with ethyl acetate. The extract was washed with dilute hydrochloric acid and with a sodium chloride aqueous solution and dried over magnesium sulfate. After treating with activated charcoal, the solvent was distilled off and the residual oil was pulverized with a mixture of diisopropyl ether and ether. The powder was collected by filtration, dried and suspended in water (150 ml.). To the suspension was added sodium bicarbonate (1.7 g.). The solution was adjusted to pH 6 with dilute hydrochloric acid and treated with activated charcoal. Dilute hydrochloric acid was added thereto with cooling and stirring and precipitates were collected by filtration, washed with water and dried to give 7-[2-ethoxycarbonyloxyimino-2-(3-hydroxyphenyl)acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (9.4 g.).

Workup

  1. stirringthe mixture was stirred for 1 hour at the same temperature
  2. washthe mixture was washed with ether
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with dilute hydrochloric acid and with a sodium chloride aqueous solution
  5. dry with materialdried over magnesium sulfate
  6. additionAfter treating with activated charcoal
  7. distillationthe solvent was distilled off
  8. additionthe residual oil was pulverized with a mixture of diisopropyl ether and ether
  9. filtrationThe powder was collected by filtration
  10. customdried
  11. additionTo the suspension was added sodium bicarbonate (1.7 g.)
  12. additiontreated with activated charcoal
  13. additionDilute hydrochloric acid was added
  14. temperaturewith cooling
  15. stirringstirring
  16. customprecipitates
  17. filtrationwere collected by filtration
  18. washwashed with water
  19. customdried

Sources & evidence

ORD record
ord-aacd5513afa74a54a67d3c94d96c8424
Source dataset
uspto-grants-1981_03
Patent number
US04254117

Reaction notes

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