Hydrochloric Acid → HCID 131714956, compound

HRID 1731696Notes

Reaction equation

HRID 1731696 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:48][O:49][CH3:50])[C:10]([NH:12][CH:13]2[C:46](=[O:47])[N:15]3[C:16]([C:30]([O:32][CH:33]([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[O:31])=[C:17]([CH2:20][S:21]/[CH:22]=[CH:23]\[C:24]4[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=O.Cl.C(=O)(O)[O-].[Na+]>CO.C(OCC)(=O)C.O>[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:48][O:49][CH3:50])[C:10]([NH:12][CH:13]2[C:46](=[O:47])[N:15]3[C:16]([C:30]([O:32][CH:33]([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)=[O:31])=[C:17]([CH2:20][S:21]/[CH:22]=[CH:23]\[C:24]4[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 131714952HCID 131714952, compound

Product 1

HCID 131714956HCID 131714956, compoundYield 90.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
35 °C

Procedure

To a suspension of benzhydryl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-[(Z)-2-(3-pyridyl)vinylthiomethyl]-3-cephem-4-carboxylate (syn isomer) (1.21 g) in methanol (24 ml) was added conc. hydrochloric acid (0.52 ml) at ambient temperature. The mixture was stirred for 1.5 hours at 35° C. The mixture was concentrated in vacuo to give a residue, which was dissolved in a mixture of ethyl acetate and water. The mixture was adjusted to pH 7 with an aqueous solution of sodium bicarbonate. The separated organic layer was washed with water and a saturated aqueous solution of sodium chloride in turn, dried over magnesium sulfate and concentrated in vacuo, and the residue was triturated in diisopropyl ether to give benzhydryl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-[(Z)-2-(3-pyridyl)vinylthiomethyl]-3-cephem-4-carboxylate (syn isomer) (1.05 g).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto give a residue, which
  3. washThe separated organic layer was washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride in turn, dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customthe residue was triturated in diisopropyl ether

Sources & evidence

ORD record
ord-6db886f78800418dbb05bec73b189b1b
Source dataset
uspto-grants-1986_11
Patent number
US04622318

Reaction notes

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