Hydrochloric Acid → HCID 131715315, compound

HRID 255785Notes

Reaction equation

HRID 255785 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:30][O:31][CH2:32][CH2:33][NH:34]C(OC(C)(C)C)=O)[C:10]([NH:12][CH:13]2[C:28](=[O:29])[N:15]3[C:16]([C:25]([OH:27])=[O:26])=[C:17]([CH2:20][O:21][C:22](=[O:24])[NH2:23])[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:30][O:31][CH2:32][CH2:33][NH2:34])[C:10]([NH:12][CH:13]2[C:28](=[O:29])[N:15]3[C:16]([C:25]([OH:27])=[O:26])=[C:17]([CH2:20][O:21][C:22](=[O:24])[NH2:23])[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131715316HCID 131715316, compound

Product 1

HCID 131715315HCID 131715315, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 7-[2-(2-formamidothiazol-4-yl)-2-(2-tert-butoxycarbonylaminoethoxyimino)acetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid (syn isomer, 1.7 g.) and conc. hydrochloric acid (1.5 g.) in methanol (30 ml.) was stirred at room temperature for 3 hours. After evaporating the solvent in vacuo, methanol was added to the residue and then evaporated in vacuo again. The residue was dissolved in water (30 ml.) and adjusted to pH 3.5 with a sodium bicarbonate saturated aqueous solution under ice-cooling. The solution was subjected to column chromatography on macroporous non-ionic adsorption resin "Diaion HP-20" (trademark, manufactured by Mitsubishi Chemical Industries Ltd.) and eluted with 30% aqueous isopropyl alcohol. The eluate was concentrated in vacuo, and the residue was lyophilized to give 7-[2-(2-aminothiazol-4-yl)-2-(2-aminoethoxyimino)acetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid (syn isomer, 1.1 g.).

Workup

  1. customAfter evaporating the solvent in vacuo, methanol
  2. additionwas added to the residue
  3. customevaporated in vacuo again
  4. dissolutionThe residue was dissolved in water (30 ml.)
  5. temperaturecooling
  6. wash" (trademark, manufactured by Mitsubishi Chemical Industries Ltd.) and eluted with 30% aqueous isopropyl alcohol
  7. concentrationThe eluate was concentrated in vacuo

Sources & evidence

ORD record
ord-a8b3d684dff84b7282df25029c0b5d50
Source dataset
uspto-grants-1987_10
Patent number
US04698337

Reaction notes

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