Acetic Acid → HCID 131712242, compound

HRID 1381363Notes

Reaction equation

HRID 1381363 reaction equation
CO.C(O)(=O)C.O.[CH3:8][O:9][N:10]=[C:11]([C:37]1[N:41]=[C:40]([NH2:42])[S:39][N:38]=1)[C:12]([NH:14][CH:15]1[C:35](=[O:36])[N:17]2[C:18]([C:22]([O:24]CC3C=CC([N+]([O-])=O)=CC=3)=[O:23])=[CH:19][CH2:20][S:21][C@H:16]12)=[O:13]>O1CCCC1.[C].[Pd]>[CH3:8][O:9][N:10]=[C:11]([C:37]1[N:41]=[C:40]([NH2:42])[S:39][N:38]=1)[C:12]([NH:14][CH:15]1[C:35](=[O:36])[N:17]2[C:18]([C:22]([OH:24])=[O:23])=[CH:19][CH2:20][S:21][C@H:16]12)=[O:13]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 962WaterHCID 131712243HCID 131712243, compound

Product 1

HCID 131712242HCID 131712242, compoundYield 54.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a mixture of tetrahydrofuran (20 ml), methanol (10 ml), acetic acid (0.25 ml) and water (2.5 ml) was dissolved 4-nitrobenzyl 7-[2-methoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-cephem-4-carboxylate (syn isomer) (0.87 g) and thereto was added 5% palladium-carbon (0.87 g). The resulting mixture was shaken under a hydrogen atmosphere at atmospheric pressure and ambient temperature for 6 hours. The reaction mixture was filtered and the filtrate was evaporated to dryness. The residue was dissolved in an aqueous solution of sodium bicarbonate and the solution was washed with ethyl acetate. The aqueous layer was adjusted to pH 2 with 10% hydrochloric acid and extracted with ethyl acetate. The extract was dried over magnesium sulfate and evaporated to dryness. The residue was triturated with diethyl ether to give the title compound (350 mg), mp. 190° to 195° C. (dec.).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated to dryness
  3. dissolutionThe residue was dissolved in an aqueous solution of sodium bicarbonate
  4. washthe solution was washed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. dry with materialThe extract was dried over magnesium sulfate
  7. customevaporated to dryness
  8. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-9216137dda304cf2847ca5d3afa95358
Source dataset
uspto-grants-1986_04
Patent number
US04585872

Reaction notes

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