Hydrochloric Acid → HCID 131713193, compound

HRID 1088146Notes

Reaction equation

HRID 1088146 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:40][O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][N:44]=2)[C:10]([NH:12][CH:13]2[C:38](=[O:39])[N:15]3[C:16]([C:22]([O:24][CH:25]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[O:23])=[C:17]([CH:20]=[CH2:21])[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=O.Cl>CO>[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:40][O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][N:44]=2)[C:10]([NH:12][CH:13]2[C:38](=[O:39])[N:15]3[C:16]([C:22]([O:24][CH:25]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)=[O:23])=[C:17]([CH:20]=[CH2:21])[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131713192HCID 131713192, compound

Product 1

HCID 131713193HCID 131713193, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of benzhydryl 7-[2-(2-formamidothiazol-4-yl)-2-(2-pyridylmethoxyimino)acetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer) (5.45 g), conc. hydrochloric acid (5 ml) and methanol (150 ml) was stirred at ambient temperature for 1.5 hours. After removal of the solvent, to the residue were added ethyl acetate and water, followed by adjusting to pH 7 with 20% aqueous sodium carbonate. The separated ethyl acetate solution was washed with an aqueous sodium chloride and then dried over anhydrous magnesium sulfate. Removal of the solvent gave benzhydryl 7-[2-(2-aminothiazol-4-yl)-2-(2-pyridylmethoxyimino)acetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer) (4.6 g).

Workup

  1. customAfter removal of the solvent
  2. additionto the residue were added ethyl acetate and water
  3. washThe separated ethyl acetate solution was washed with an aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-cf49d1b3022943ab9ad4cca2e3e5fdc1
Source dataset
uspto-grants-1990_10
Patent number
US04960889

Reaction notes

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