Hydrochloric Acid → HCID 131714359, compound

HRID 980982Notes

Reaction equation

HRID 980982 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:41]1[N:42]=[C:43]([NH:46]C=O)[S:44][CH:45]=1)[C:5]([NH:7][CH:8]1[C:39](=[O:40])[N:10]2[C:11]([C:23]([O:25][CH:26]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])=[C:12]([CH:15]=[CH:16][C:17]3[N:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH2:13][S:14][C@H:9]12)=[O:6].Cl.C(=O)(O)[O-].[Na+]>CO.O1CCCC1>[CH3:1][O:2][N:3]=[C:4]([C:41]1[N:42]=[C:43]([NH2:46])[S:44][CH:45]=1)[C:5]([NH:7][CH:8]1[C:39](=[O:40])[N:10]2[C:11]([C:23]([O:25][CH:26]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:24])=[C:12]([CH:15]=[CH:16][C:17]3[N:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 131714358HCID 131714358, compound

Product 1

HCID 131714359HCID 131714359, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzhydryl 7-[2-methoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-[2-(3-pyridazinyl)vinyl]-3-cephem-4-carboxylate (syn isomer) (trans isomer) (0.85 g) in methanol (45 ml) and tetrahydrofuran (9 ml) was added conc.hydrochloric acid (0.56 ml) and the mixture was stirred at ambient temperature for 1.5 hours. The resultant solution was adjusted to pH 7.0 with 5% aqueous sodium bicarbonate and concentrated under reduced pressure. The residue was dissolved in ethyl acetate (150 ml). The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated in vacuo to give benzhydryl 7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[2-(3-pyridazinyl)vinyl]-3-cephem-4-carboxylate (syn isomer) (trans isomer) (0.68 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate (150 ml)
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-005f4de7cd6f4418a71aa48e7af9b35b
Source dataset
uspto-grants-1987_01
Patent number
US04639448

Reaction notes

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