Hydrochloric Acid → HCID 131714634, compound

HRID 1380968Notes

Reaction equation

HRID 1380968 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:42]1[N:43]=[C:44]([NH:47]C=O)[S:45][CH:46]=1)[C:5]([NH:7][CH:8]1[C:40](=[O:41])[N:10]2[C:11]([C:24]([O:26]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:25])=[C:12]([CH:15]=[CH:16][S:17][C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[CH2:13][S:14][C@H:9]12)=[O:6].Cl.C(=O)(O)[O-].[Na+].C1(OC)C=CC=CC=1.C(OC(C)C)(C)C>CO.ClCCl.C(OCC)(=O)C.O>[CH3:1][O:2][N:3]=[C:4]([C:42]1[N:43]=[C:44]([NH2:47])[S:45][CH:46]=1)[C:5]([NH:7][CH:8]1[C:40](=[O:41])[N:10]2[C:11]([C:24]([OH:26])=[O:25])=[C:12]([CH:15]=[CH:16][S:17][C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 7914Diisopropyl EtherHCID 516892Sodium BicarbonateHCID 131714635HCID 131714635, compound

Product 1

HCID 131714634HCID 131714634, compoundYield 4.8%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzhydryl 7-[2-metoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-[2-(3-pyridyl)thiovinyl]-3-cephem-4-carboxylate (syn isomer) (trans isomer) (2 g) in methanol (20 ml) was added conc. hydrochloric acid (0.85 ml) at ambient temperature and the resultant mixture was stirred at 25°-30° C. for 2 hours. Water and ethyl acetate were added to the reaction mixture and the resultant mixture was adjusted to pH 7.0 with saturated aqueous sodium bicarbonate. The separated organic layer was evaporated in vacuo to give a yellowish residue. A mixture of this residue and trifuluoroacetic acid (5 ml) containing anisole (1 ml) in dichloromethane (10 ml) was stirred at 5°-10° C. for an hour. The mixture was poured into diisopropyl ether (100 ml) to give precipitate, which was collected by filtration and dissolved in 5% aqueous sodium bicarbonate at pH 5.5. The resulting solution was chromatographed on macropourous non-ionic resin "Diaion-HP-20" and eluted with 20% aqueous solution of isopropyl alcohol. The fractions containing object compound were concentrated and acidified at pH 2.2 with conc. hydrochloric acid to give 7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[2-(3-pyridyl)thiovinyl]-3-cephem-4-carboxylic acid (syn isomer) (trans isomer) (0.07 g).

Workup

  1. customThe separated organic layer was evaporated in vacuo
  2. customto give a yellowish residue
  3. customto give precipitate, which
  4. filtrationwas collected by filtration
  5. dissolutiondissolved in 5% aqueous sodium bicarbonate at pH 5.5
  6. customThe resulting solution was chromatographed on macropourous non-ionic resin "
  7. wash" and eluted with 20% aqueous solution of isopropyl alcohol
  8. additionThe fractions containing object compound
  9. concentrationwere concentrated

Sources & evidence

ORD record
ord-714eea2898b9437e942a7724a01c8ae8
Source dataset
uspto-grants-1986_04
Patent number
US04584290

Reaction notes

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