Hydrochloric Acid → HCID 131714845, compound

HRID 64752Notes

Reaction equation

HRID 64752 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:37]1[N:38]=[C:39]([NH:42]C=O)[S:40][CH:41]=1)[C:5]([NH:7][CH:8]1[C:35](=[O:36])[N:10]2[C:11]([C:19]([O:21][CH:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])=[C:12]([CH:15]=[C:16]([Cl:18])[Cl:17])[CH2:13][S:14][C@H:9]12)=[O:6].Cl.O.C(=O)(O)[O-].[Na+]>CO.C(OCC)(=O)C>[CH3:1][O:2][N:3]=[C:4]([C:37]1[N:38]=[C:39]([NH2:42])[S:40][CH:41]=1)[C:5]([NH:7][CH:8]1[C:35](=[O:36])[N:10]2[C:11]([C:19]([O:21][CH:22]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])=[C:12]([CH:15]=[C:16]([Cl:18])[Cl:17])[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 131714844Benzhydryl 7-[2-methoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(2,2-dichlorovinyl)-3-cephem-4-carboxylate

Product 1

HCID 131714845HCID 131714845, compoundYield 93.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzhydryl 7-[2-methoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(2,2-dichlorovinyl)-3-cephem-4-carboxylate (syn isomer) (2.2 g) in methanol (11 ml) was added conc. hydrochloric acid (0.72 ml) and the resulting mixture was stirred at ambient temperature for 3 hours. To the reaction mixture were added water and ethyl acetate, the mixture was adjusted to pH 7.0 with saturated aqueous sodium bicarbonate, the separated organic layer was washed with brine, dried over magnesium sulfate. The solution was evaporated in vacuo to give benzhydryl 7-[2-methoxyimino-2-(2-aminothiazol-4-yl)-acetamido]-3-(2,2-dichlorovinyl)-3-cephem-4-carboxylate (syn isomer) (1.98 g).

Workup

  1. washthe separated organic layer was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solution was evaporated in vacuo

Sources & evidence

ORD record
ord-c8d0286ad09e4cd48aa7238c9b037bba
Source dataset
uspto-grants-1986_09
Patent number
US04609730

Reaction notes

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