Hydrochloric Acid → HCID 178502835, compound

HRID 1707475Notes

Reaction equation

HRID 1707475 reaction equation
C1(C([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:45])[C@@H:24]([NH:25][C:26](=[O:44])/[C:27](/[C:31]4[N:32]=[C:33]([NH:36]C(OC(C)(C)C)=O)[S:34][CH:35]=4)=[N:28]\[O:29][CH3:30])[C@H:21]3[S:20][CH2:19][C:18]=2[CH2:46][S:47][C:48]2[N:49]=[N:50][N:51](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:52]=2)=[S:16])C2C=CC=CC=2)C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl.C(=O)([O-])O.[Na+:81]>C1(OC)C=CC=CC=1.[N+](C)([O-])=O.O.C(OCC)(=O)C>[Na+:81].[NH2:36][C:33]1[S:34][CH:35]=[C:31](/[C:27](=[N:28]/[O:29][CH3:30])/[C:26]([NH:25][C@@H:24]2[C:23](=[O:45])[N:22]3[C:17]([C:15]([O-:14])=[S:16])=[C:18]([CH2:46][S:47][C:48]4[N:49]=[N:50][NH:51][CH:52]=4)[CH2:19][S:20][C@H:21]23)=[O:44])[N:32]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) ChlorideHCID 141566144HCID 141566144, compound

Product 1

HCID 178502835HCID 178502835, compoundYield 66%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6375NitromethaneSolventHCID 7519AnisoleSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-methoxyiminoacetyl]amino-3-(1-trityl-1,2,3-triazol-4-yl)thiomethylthio-3-cephem-4-carboxylic acid diphenylmethyl ester (570 mg: 0.55 mMol.) in a mixture of anisole (1.7 ml) and nitromethane (5 ml) at -30° C. is added e solution of aluminum chloride (0.51 g: 3.83 mMol.) in anisole (1.8 ml), and the mixture is stirred for 30 minutes. The reaction mixture is mixed with 1N-hydrochloric acid (4 ml) and ethyl acetate (10 ml), stirred at room temperature for 5 minutes, poured into a solution of sodium hydrogen carbonate (3.2 g) in water (100 ml), and stirred for several minutes. After filtering off the insoluble material, the reaction mixture is washed with ethyl acetate, concentrated in vacuum to remove the organic solvents. The resulting aqueous layer is purified by stylene-divinylbenzene copolymer chromatography (water: methanol=10:1) to give 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetyl]amino-3-(1,2,3-triazol-4-yl)thiomethylthio-3-cephem-4-carboxylic acid sodium salt as white foam (194 mg). Yield: 64%.

Workup

  1. stirringstirred at room temperature for 5 minutes
  2. stirringstirred for several minutes
  3. filtrationAfter filtering off the insoluble material
  4. washthe reaction mixture is washed with ethyl acetate
  5. concentrationconcentrated in vacuum
  6. customto remove the organic solvents
  7. customThe resulting aqueous layer is purified by stylene-divinylbenzene copolymer chromatography (water: methanol=10:1)

Sources & evidence

ORD record
ord-d26a9a4956694bda9b83daed811f93a7
Source dataset
uspto-grants-1994_10
Patent number
US05352792

Reaction notes

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