Hydrochloric Acid → HCID 131713119, compound

HRID 647119Notes

Reaction equation

HRID 647119 reaction equation
C([O:5][C:6]([CH2:8][O:9][N:10]=[C:11]([C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([NH2:40])[N:35]=1)[C:12]([NH:14][CH:15]1[C:32](=[O:33])[N:17]2[C:18]([C:29]([O-:31])=[O:30])=[C:19]([CH2:22][N+:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:20][S:21][C@H:16]12)=[O:13])=[O:7])(C)(C)C.Cl>C(O)=O>[C:6]([CH2:8][O:9][N:10]=[C:11]([C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([NH2:40])[N:35]=1)[C:12]([NH:14][CH:15]1[C:32](=[O:33])[N:17]2[C:18]([C:29]([O-:31])=[O:30])=[C:19]([CH2:22][N+:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:20][S:21][C@H:16]12)=[O:13])([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131713121HCID 131713121, compound

Product 1

HCID 131713119HCID 131713119, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To a solution of 7-[2-tert-butoxycarbonylmethoxyimino-2-(6-aminopyridin-2-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (5.0 g) in formic acid (50 ml) was added conc. hydrochloric acid (2 ml), and the mixture was stirred at ambient temperature for an hour. After the solvent was removed by distillation under reduced pressure, the residue was dissolved in water (100 ml), followed by subjecting to column chromatography on a non-ionic adsorption resin, "Diaion HP-20" (200 ml). After the column was washed with water (600 ml), elution was carried out with 10% aqueous methanol. The eluates containing a desired compound were collected, evaporated to remove methanol under reduced pressure and then lyophilized to obtain 7-[2-carboxymethoxyimino-2-(6-aminopyridin-2-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (3.0 g), mp 100° to 108° C. (dec.).

Workup

  1. customAfter the solvent was removed by distillation under reduced pressure
  2. dissolutionthe residue was dissolved in water (100 ml)
  3. washAfter the column was washed with water (600 ml), elution
  4. additionThe eluates containing a desired compound
  5. customwere collected
  6. customevaporated
  7. customto remove methanol under reduced pressure

Sources & evidence

ORD record
ord-67186c9f4eaf48fa998cbad3ed2a3fe2
Source dataset
uspto-grants-1983_10
Patent number
US04407798

Reaction notes

Loading…