HCID 88389564, compound → HCID 13193157, compound

HRID 1389888Notes

Reaction equation

HRID 1389888 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:42](=[O:43])[N:13]3[C:14]([C:29]([O:31]CC4C=CC([N+]([O-])=O)=CC=4)=[O:30])=[C:15](OS(C4C=CC(C)=CC=4)(=O)=O)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)=O.[Zn]>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:42](=[O:43])[N:13]3[C:14]([C:29]([OH:31])=[O:30])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 88389564HCID 88389564, compound

Product 1

HCID 13193157HCID 13193157, compoundYield 71.5%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 284Formic AcidSolvent

Procedure

Zinc powder (2.0 g.) was added portionwise to a stirred solution of 4-nitrobenzyl 7-(2-phenylacetamido)-3-tosyloxy-3-cephem-4-carboxylate (2.0 g.) in 90% formic acid (40 ml.) over 6 minutes under ice-cooling. The mixture was stirred at room temperature for an hour and then filtered. The remaining insoluble substances were washed with ethyl acetate. The filtrate and the washings were combined together and evaporated in vacuo. The residue was dissolved in ethyl acetate, washed with water, diluted hydrochloric acid and water in turn, dried over magnesium sulfate and then evaporated to dryness in vacuo. The oily residue was pulverized by trituration with diisopropyl ether and the solidified precipitates were collected by filtration to give 7-(2-phenylacetamido)-3-cephem-4-carboxylic acid (0.73 g.), Yield 71.5%.

Workup

  1. temperaturecooling
  2. filtrationfiltered
  3. washThe remaining insoluble substances were washed with ethyl acetate
  4. customevaporated in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with water, diluted hydrochloric acid and water in turn
  7. dry with materialdried over magnesium sulfate
  8. customevaporated to dryness in vacuo
  9. customthe solidified precipitates
  10. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-e1f3135a885e42dbbb72a773237a411f
Source dataset
uspto-grants-1981_01
Patent number
US04246405

Reaction notes

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