Hydrochloric Acid → HCID 131713928, compound

HRID 1632762Notes

Reaction equation

HRID 1632762 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:34][O:35][CH3:36])[C:10]([NH:12][CH:13]2[C:32](=[O:33])[N:15]3[C:16]([C:20]([O:22][CH:23]([CH2:28][O:29][CH2:30][CH3:31])[CH2:24][O:25][CH2:26][CH3:27])=[O:21])=[CH:17][CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=O.Cl.C(=O)(O)[O-].[Na+]>CO>[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:34][O:35][CH3:36])[C:10]([NH:12][CH:13]2[C:32](=[O:33])[N:15]3[C:16]([C:20]([O:22][CH:23]([CH2:28][O:29][CH2:30][CH3:31])[CH2:24][O:25][CH2:26][CH3:27])=[O:21])=[CH:17][CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 131713929HCID 131713929, compound

Product 1

HCID 131713928HCID 131713928, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-ethoxy-1-ethoxymethylethyl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 2.85 g) in methanol (57 ml) was slowly added conc. hydrochloric acid (1.13 ml) at room temperature, and stirred at room temperature for 3 hours. The resultant mixture was poured into ice water (280 ml), adjusted to pH 7 to 8 with an aqueous solution of sodium bicarbonate, and then extracted with ethyl acetate (150 ml). The extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, the residue was subjected to column chromatography on silica gel with a mixture of chloroform and methaol (30:1). The eluate was concentrated under reduced pressure to give 2-ethoxy-1-ethoxymethylethyl 7-[2-(2-aminothiazol-4-yl]-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 1.77 g), mp. 95° to 97° C.

Workup

  1. customat room temperature
  2. extractionextracted with ethyl acetate (150 ml)
  3. washThe extract was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter the solvent was evaporated under reduced pressure
  6. additionthe residue was subjected to column chromatography on silica gel with a mixture of chloroform and methaol (30:1)
  7. concentrationThe eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5de2b7a6dca0441e8c4f511631365dae
Source dataset
uspto-grants-1984_10
Patent number
US04477447

Reaction notes

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