Chloro-N,N-dimethylformiminium chloride → 7-[2-(2-Cyclopenten-1-yl)oxyimino-2-(2-formamidothiazol-4-yl)acetamido]-2-methyl-3-cephem-4-carboxylic acid

HRID 1074939Notes

Reaction equation

HRID 1074939 reaction equation
[CH:1]1([O:6][N:7]=[C:8]([C:12]2[N:13]=[C:14]([NH:17][CH:18]=[O:19])[S:15][CH:16]=2)[C:9]([OH:11])=O)[CH2:5][CH2:4][CH:3]=[CH:2]1.C[N+](C)=CCl.[Cl-].[NH2:26][CH:27]1[C:38](=[O:39])[N:29]2[C:30]([C:35]([OH:37])=[O:36])=[CH:31][CH:32]([CH3:34])[S:33][C@H:28]12.C[Si](CC(N)=O)(C)C>O1CCCC1.C(OCC)(=O)C.O>[CH:1]1([O:6][N:7]=[C:8]([C:12]2[N:13]=[C:14]([NH:17][CH:18]=[O:19])[S:15][CH:16]=2)[C:9]([NH:26][CH:27]2[C:38](=[O:39])[N:29]3[C:30]([C:35]([OH:37])=[O:36])=[CH:31][CH:32]([CH3:34])[S:33][C@H:28]23)=[O:11])[CH2:5][CH2:4][CH:3]=[CH:2]1

Participants

8

Reactant 4

HCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 128022512-Methyl-7-amino-3-cephem-4-carboxylic acidHCID 538228722-(2-Cyclopenten-1-yl)oxyimino-2-(2-formamidothiazol-4-yl)acetic acid

Product 1

HCID 1317130257-[2-(2-Cyclopenten-1-yl)oxyimino-2-(2-formamidothiazol-4-yl)acetamido]-2-methyl-3-cephem-4-carboxylic acidYield 77.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 2-(2-cyclopenten-1-yl)oxyimino-2-(2-formamidothiazol-4-yl)acetic acid (syn isomer) (1.5 g) in dry tetrahydrofuran (12 ml) was added to the stirred suspension of the solution of Vilsmeier reagent under ice-cooling. The resulting mixture was added to a solution of 7-amino-2-methyl-3-cephem-4-carboxylic acid (1.37 g) and trimethylsilylacetamide (5.04 g) in ethyl acetate (14 ml) at -30° to -20° C. and the mixture was stirred at -5°~-10° C. for 2 hours. After the addition of water and ethyl acetate to the reaction mixture, the ethyl acetate layer was separated and adjusted to pH 7 with an aqueous solution of sodium bicarbonate. The aqueous layer was separated and thereto was added ethyl acetate. The mixture was adjusted to pH 2.5 with 10% hydrochloric acid. The ethyl acetate layer was separated, washed with an aqueous solution of sodium chloride, dried over magnesium sulfate and then evaporated. The residue was pulverized in diisopropyl ether to give 7-[2-(2-cyclopenten-1-yl)oxyimino-2-(2-formamidothiazol-4-yl)acetamido]-2-methyl-3-cephem-4-carboxylic acid (syn isomer) (1.98 g).

Workup

  1. temperaturecooling
  2. customthe ethyl acetate layer was separated
  3. customThe aqueous layer was separated
  4. additionwas added ethyl acetate
  5. customThe ethyl acetate layer was separated
  6. washwashed with an aqueous solution of sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-17f347830ccc46768070c1b54a100b40
Source dataset
uspto-grants-1983_07
Patent number
US04394384

Reaction notes

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