Hydrochloric Acid → HCID 131715952, compound

HRID 1762688Notes

Reaction equation

HRID 1762688 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:28][O:29][CH3:30])[C:8]([NH:10][C@@H:11]2[C:26](=[O:27])[N:13]3[C:14]([C:23]([O-:25])=[O:24])=[C:15]([CH2:18]OC(=O)C)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[Na+].[I-].[Na+].[O:34]1[CH:38]=[CH:37][N:36]=[C:35]1[C:39]1[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=1.Cl>CC(C)=O.C(#N)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:28][O:29][CH3:30])[C:8]([NH:10][C@@H:11]2[C:26](=[O:27])[N:13]3[C:14]([C:23]([O-:25])=[O:24])=[C:15]([CH2:18][N+:42]4[CH:41]=[CH:40][C:39]([C:35]5[O:34][CH:38]=[CH:37][N:36]=5)=[CH:44][CH:43]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 3752778Pyridine, 4-(2-oxazolyl)-HCID 23675341HCID 23675341, compound

Product 1

HCID 131715952HCID 131715952, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

0.75 g of sodium 7β-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-acetoxymethyl-3-cephem-4-carboxylate (hereinafter referred to Compound 1), 2.25 g of sodium iodide and 0.51 g of 4-(oxazol-2-yl)-pyridine were added to a mixture of 0.4 ml of 4 N hydrochloric acid and 1.2 ml of acetonitrile, followed by stirring at 80° C. for 1 hour. After allowing the mixture to cool, the reaction mixture was poured into acetone, and the precipitate formed was separated by filtration and washed with acetone. The resulting crude powder was dissolved in water, and the solution was subjected to column chromatography of Diaion HP-20 (trade name of Mitsubishi Chemical Industries, Ltd.). The column was developed with a mixture of water-tetrahydrofuran (93:7 by volume). The eluate was further subjected to reversed phase high performance liquid chromatography (column packing: Develosil, trade name of Nomura Chemical Co., Ltd.) and developed with a mixture of water-acetonitrile (89:11 by volume) to obtain the titled compound. Melting point: 160°-170° C. (decomposition).

Workup

  1. temperatureto cool
  2. customthe precipitate formed
  3. customwas separated by filtration
  4. washwashed with acetone
  5. dissolutionThe resulting crude powder was dissolved in water
  6. additionThe column was developed with a mixture of water-tetrahydrofuran (93:7 by volume)
  7. additiondeveloped with a mixture of water-acetonitrile (89:11 by volume)

Sources & evidence

ORD record
ord-52debf76abc64562b3357f55012ae191
Source dataset
uspto-grants-1989_05
Patent number
US04833242

Reaction notes

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