Hydrochloric Acid → 7-[2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetamido]-3-[3-(4-carbamoylpyridinio)-1-propenyl]-3-cephem-4-carboxylate

HRID 580206Notes

Reaction equation

HRID 580206 reaction equation
Cl.[NH2:2][CH:3]1[C:25](=[O:26])[N:5]2[C:6]([C:22]([OH:24])=[O:23])=[C:7](/[CH:10]=[CH:11]/[CH2:12][N+:13]3[CH:18]=[CH:17][C:16]([C:19](=[O:21])[NH2:20])=[CH:15][CH:14]=3)[CH2:8][S:9][C@H:4]12.C([O-])(O)=O.[Na+].N1([CH2:41][O:42][N:43]=[C:44]([C:48]2[N:52]=[C:51]([NH2:53])[S:50][N:49]=2)[C:45]([O-])=[O:46])C2C=CC=CC=2N=N1.Cl>CN(C=O)C.CC(C)=O>[NH2:53][C:51]1[S:50][N:49]=[C:48]([C:44](=[N:43][O:42][CH3:41])[C:45]([NH:2][CH:3]2[C:25](=[O:26])[N:5]3[C:6]([C:22]([O-:24])=[O:23])=[C:7]([CH:10]=[CH:11][CH2:12][N+:13]4[CH:14]=[CH:15][C:16]([C:19](=[O:21])[NH2:20])=[CH:17][CH:18]=4)[CH2:8][S:9][C@H:4]23)=[O:46])[N:52]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 1317156027-amino-3-[3-(4-carbamoylpyridinio)-1-(E)-propenyl]-3-cephem-4-carboxylic acid hydrochlorideHCID 131715603Benzotriazol-1-yl-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetate

Product 1

HCID 1317155907-[2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetamido]-3-[3-(4-carbamoylpyridinio)-1-propenyl]-3-cephem-4-carboxylate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 7-amino-3-[3-(4-carbamoylpyridinio)-1-(E)-propenyl]-3-cephem-4-carboxylic acid hydrochloride (XXII-H, 397 mg, 1 mmole) and NaHCO3 (168 mg, 2 mmoles) in aqueous DMF (water, 3.5 ml and DMF, 7.5 ml) was added benzotriazol-1-yl-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetate (479 mg, 1.5 mmoles) (from Preparation No. 28). The mixture was stirred at room temperature for 3.5 hours. The reaction mixture was adjusted to pH 3-4 with 3N HCl and diluted with 200 ml of acetone to give a precipitate, which was collected by filtration. The crude product was dissolved in a small volume of aqueous THF and the solution was adjusted to pH 6.8 with NaHCO3, treated with decolorizing carbon, concentrated to ca. 1 ml and seeded with a few pieces of crystalline I-1H. After stirring overnight, the crystalline precipitate was collected by filtration to afford the title compound I-1H (zwitterion form). Yield 83 mg (16%). Mp. >185° C. (dec.). Physico-chemical data of this product were identical to those of the compound in Example 10.

Workup

  1. customto give a precipitate, which
  2. filtrationwas collected by filtration
  3. dissolutionThe crude product was dissolved in a small volume of aqueous THF
  4. additiontreated with decolorizing carbon
  5. concentrationconcentrated to ca. 1 ml
  6. stirringAfter stirring overnight
  7. filtrationthe crystalline precipitate was collected by filtration

Sources & evidence

ORD record
ord-4706b97dcaab426c8dc2a7695879bbd0
Source dataset
uspto-grants-1988_06
Patent number
US04751295

Reaction notes

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