Methane → HCID 131713922, compound

HRID 1632758Notes

Reaction equation

HRID 1632758 reaction equation
Cl.C([NH:4][C:5]1[S:6][CH:7]=[C:8]([C:10](=[N:30][O:31][CH3:32])[C:11]([NH:13][CH:14]2[C:28](=[O:29])[N:16]3[C:17]([C:21]([O:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:22])=[CH:18][CH2:19][S:20][C@H:15]23)=[O:12])[N:9]=1)=O.[OH-].[Na+].C>CO.O>[NH2:4][C:5]1[S:6][CH:7]=[C:8]([C:10](=[N:30][O:31][CH3:32])[C:11]([NH:13][CH:14]2[C:28](=[O:29])[N:16]3[C:17]([C:21]([O:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:22])=[CH:18][CH2:19][S:20][C@H:15]23)=[O:12])[N:9]=1

Participants

7

Reactant 4

HCID 297MethaneHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131713923HCID 131713923, compound

Product 1

HCID 131713922HCID 131713922, compoundYield 92.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Conc-Hydrochloric acid (4 ml) was dropwise added to a suspension of n-butyl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 7.5 g) in methanol (120 ml) over 5 minutes under ice cooling, and stirred at room temperature for 4.25 hours. The resultant solution was poured into chilled water (75 ml), and adjusted to pH 5.5 with 4N aqueous solution of sodium hydroxide at 5° C. After treating the solution with activated charcoal (0.38 g), the solution was concentrated in vacuo. The aqueous residue was stirred under ice cooling for 30 minutes. The precipitates were collected by filtration, washed with water (10 ml×2), and then dried over phosphorus pentoxide to give yellow powder (6.55 g) of n-butyl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer).

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. stirringThe aqueous residue was stirred under ice cooling for 30 minutes
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with water (10 ml×2)
  5. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-e1765637d58645fcb4ffece5cd9322e9
Source dataset
uspto-grants-1984_10
Patent number
US04477447

Reaction notes

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