HCID 88764022, compound → HCID 13193157, compound

HRID 1389887Notes

Reaction equation

HRID 1389887 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:37](=[O:38])[N:13]3[C:14]([C:29]([O:31]CC(Cl)(Cl)Cl)=[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:37](=[O:38])[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 88764022HCID 88764022, compound

Product 1

HCID 13193157HCID 13193157, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 284Formic AcidSolvent

Procedure

Zinc powder (4.0 g.) was added portionwise to a stirred solution of 2,2,2-trichloroethyl 7-(2-phenylacetamido)-3-tosyloxy-3-cephem-4-carboxylate (0.8 g.) in formic acid (16 ml.) over 3 minutes under ice-cooling. The mixture was stirred at the same temperature for 5 minutes and then filtered. The remaining zinc powder was washed with ethyl acetate. The filtrate and washings were combined together, washed three times with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and then evaporated to dryness in vacuo. The residue was pulverized by trituration with diisopropyl ether and the precipitates were collected by filtration to give 7-(2-phenylacetamido)-3-cephem-4-carboxylic acid (0.32 g.), Yield 78.1%.

Workup

  1. temperaturecooling
  2. filtrationfiltered
  3. washThe remaining zinc powder was washed with ethyl acetate
  4. washwashed three times with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness in vacuo
  7. filtrationthe precipitates were collected by filtration

Sources & evidence

ORD record
ord-2a07dc0d11884ffd952706ac115abdba
Source dataset
uspto-grants-1981_01
Patent number
US04246405

Reaction notes

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