Hydrochloric Acid → HCID 131714763, compound

HRID 1982674Notes

Reaction equation

HRID 1982674 reaction equation
C[N+](C)=CCl.[Cl-].P(Cl)(Cl)(Cl)=O.[CH:12]([NH:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]([C:21](=[N:25][O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:22]([OH:24])=O)[N:16]=1)=[O:13].[NH2:33][CH:34]1[C:51](=[O:52])[N:36]2[C:37]([C:48]([OH:50])=[O:49])=[C:38]([CH2:41][S:42][C:43]3[S:44][CH:45]=[N:46][N:47]=3)[CH2:39][S:40][C@H:35]12.C[Si](CC(N)=O)(C)C.C(=O)(O)[O-].[Na+].Cl>C(Cl)Cl.CC(C)=O.C(OCC)(=O)C.CN(C)C=O>[CH:12]([NH:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]([C:21](=[N:25][O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:22]([NH:33][CH:34]2[C:51](=[O:52])[N:36]3[C:37]([C:48]([OH:50])=[O:49])=[C:38]([CH2:41][S:42][C:43]4[S:44][CH:45]=[N:46][N:47]=4)[CH2:39][S:40][C@H:35]23)=[O:24])[N:16]=1)=[O:13]

Participants

12

Reactant 7

HCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 516892Sodium BicarbonateHCID 128891877-Amino-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3cephem-4-carboxylic acidHCID 54570484HCID 54570484, compound

Product 1

HCID 131714763HCID 131714763, compoundYield 69.3%

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

Methylene chloride (15 ml) was added to a Vilsmeier reagent, which was prepared by phosphoryl chloride (0.75 g) and N,N-dimethylformamide (0.75 ml) in a conventional manner. To this mixture was added 2-(4-formamidopyrimidin-2-yl)-2-phenoxyiminoacetic acid (syn isomer) (1.0 g) at -20° C., followed by stirring at -15° to -13° C. for half an hour. To this solution was added a solution of 7-amino-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid (1.27 g) and trimethylsilylacetamide (4.6 g) in methylene chloride (14 ml) at -20° C. with stirring, and the stirring was continued at -15° to -13° C. for half an hour and at ambient temperature for additional half an hour. The reaction mixture was evaporated to give a residue, to which ethyl acetate and then an aqueous solution of sodium bicarbonate were added. To the separated aqueous solution was added ethyl acetate and then adjusted to pH 1 to 2 with hydrochloric acid. After addition of a small amount of acetone, the organic layer was separated, washed with water and an aqueous solution of sodium chloride, dried over magnesium sulfate, and then evaporated. The residue was pulverized with diethyl ether to give 7-[2-(4-formamidopyrimidin-2-yl)-2-phenoxyiminoacetamido]-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid (syn isomer) (1.45 g).

Workup

  1. stirringwith stirring
  2. waitthe stirring was continued at -15° to -13° C. for half an hour and at ambient temperature for additional half an hour
  3. customThe reaction mixture was evaporated
  4. customto give a residue
  5. customthe organic layer was separated
  6. washwashed with water
  7. dry with materialan aqueous solution of sodium chloride, dried over magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-86859c4a67084b859a9ae0d9c7552785
Source dataset
uspto-grants-1986_06
Patent number
US04596869

Reaction notes

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