Hydrochloric Acid → 7-[2-(2-Aminothiazol-4-yl)-2-(3-aminopropoxyimino)-acetamido]-3-cephem-4-carboxylic acid

HRID 745427Notes

Reaction equation

HRID 745427 reaction equation
Cl.C([NH:4][C:5]1[S:6][CH:7]=[C:8]([C:10](=[N:26][O:27][CH2:28][CH2:29][CH2:30][NH:31]C(OC(C)(C)C)=O)[C:11]([NH:13][CH:14]2[C:24](=[O:25])[N:16]3[C:17]([C:21]([OH:23])=[O:22])=[CH:18][CH2:19][S:20][C@H:15]23)=[O:12])[N:9]=1)=O>CO>[NH2:4][C:5]1[S:6][CH:7]=[C:8]([C:10](=[N:26][O:27][CH2:28][CH2:29][CH2:30][NH2:31])[C:11]([NH:13][CH:14]2[C:24](=[O:25])[N:16]3[C:17]([C:21]([OH:23])=[O:22])=[CH:18][CH2:19][S:20][C@H:15]23)=[O:12])[N:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1317123497-[2-(2-Formamidothiazol-4-yl)-2-(3-tert-butoxycarbonylaminopropoxyimino)acetamido]-3-cephem-4-carboxylic acid

Product 1

HCID 1317123507-[2-(2-Aminothiazol-4-yl)-2-(3-aminopropoxyimino)-acetamido]-3-cephem-4-carboxylic acidYield 61.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Conc.hydrochloric acid (1.6 ml.) was added to a solution of 7-[2-(2-formamidothiazol-4-yl)-2-(3-tert-butoxycarbonylaminopropoxyimino)acetamido]-3-cephem-4-carboxylic acid (syn isomer, 2.1 g.) in methanol (30 ml.), and stirred at room temperature for 3.5 hours. After evaporating the solvent in vacuo, methanol was added to the residue and the mixture was 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 lyophilized to give 7-[2-(2-aminothiazol-4-yl)-2-(3-aminopropoxyimino)-acetamido]-3-cephem-4-carboxylic acid (syn isomer, 1.0 g.).

Workup

  1. customAfter evaporating the solvent in vacuo, methanol
  2. additionwas added to the residue
  3. customthe mixture was evaporated 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-fa14a368123742959d23156842654892
Source dataset
uspto-grants-1986_07
Patent number
US04598147

Reaction notes

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