HCID 88683653, compound → HCID 88683896, compound

HRID 1164429Notes

Reaction equation

HRID 1164429 reaction equation
[CH3:1][O:2][N:3]([CH:14]1[C:30](=[O:31])[N:16]2[C:17]([C:22]([O:24]CC(Cl)(Cl)Cl)=[O:23])=[C:18]([CH3:21])[CH2:19][S:20][C@H:15]12)[C:4](=[O:13])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(Cl)Cl.C(O)(=O)C.CN(C)C=O.C(OCC)(=O)C.[Zn]>[CH3:1][O:2][N:3]([CH:14]1[C:30](=[O:31])[N:16]2[C:17]([C:22]([OH:24])=[O:23])=[C:18]([CH3:21])[CH2:19][S:20][C@H:15]12)[C:4](=[O:13])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 1

HCID 88683653HCID 88683653, compound

Product 1

HCID 88683896HCID 88683896, compoundYield 38.8%

Reagents, catalysts & solvents 5

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent2×HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2,2,2-Trichloroethyl 7-(N-methoxy-2-phenoxyacetamido)-3-methyl-3-cephem-4-carboxylate (490 mg) is dissolved in a mixture of methylene chloride (15 ml), acetic acid (4 ml) and dimethylformamide (4 ml), and under ice-cooling, zinc dust (400 mg) is added. The mixture is stirred at room temperature for 1.5 hours, at the end of which time acetic acid (10 ml), dimethylformamide (2 ml) and zinc dust (300 mg) are further added and stirred for another 1.5 hours. The reaction mixture is diluted with ethyl acetate and filtered. The filtrate is washed with 0.5 N-HCl and aqueous sodium chloride in that order, dried over magnesium sulfate and concentrated. The resultant crude crystals are washed with ether-ethyl acetate to give 7-(N-methoxy-2-phenoxyacetamido)-3-methyl-3-cephem-4-carboxylic acid (141 mg).

Workup

  1. temperatureunder ice-cooling
  2. additionare further added
  3. filtrationfiltered
  4. washThe filtrate is washed with 0.5 N-HCl and aqueous sodium chloride in that order
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. washThe resultant crude crystals are washed with ether-ethyl acetate

Sources & evidence

ORD record
ord-4f9557d9b9014585a54a4c35ef0e93b1
Source dataset
uspto-grants-1983_01
Patent number
US04369312

Reaction notes

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