HCID 177726213, compound → HCID 177719161, compound

HRID 1463150Notes

Reaction equation

HRID 1463150 reaction equation
[C:1]1(/[C:7](=[N:41]/[O:42][CH3:43])/[C:8]([NH:10][CH:11]2[C:39](=[O:40])[N:13]3[C:14]([C:23]([O:25]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:24])=[C:15]([CH:19]=[N:20][O:21][CH3:22])[C@@H:16]([CH3:18])[S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C1(OC)C=CC=CC=1.C(O)(C(F)(F)F)=O>[C:1]1(/[C:7](=[N:41]/[O:42][CH3:43])/[C:8]([NH:10][CH:11]2[C:39](=[O:40])[N:13]3[C:14]([C:23]([OH:25])=[O:24])=[C:15]([CH:19]=[N:20][O:21][CH3:22])[C@@H:16]([CH3:18])[S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 177726213HCID 177726213, compound

Product 1

HCID 177719161HCID 177719161, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

A solution of 294 mg of diphenylmethyl 7-[2-phenyl-(Z)-2-methoxyiminoacetamido]-2α-methyl-3-methoxyiminomethylceph-3-em-4-carboxylate in 0.3 ml of anisole and 10 ml of CF3COOH was stirred at room temperature for 20 minutes. After distilling off the CF3COOH under reduced pressure, the residue was dissolved in AcOEt and then transferred into 5% aqueous NaHCO3. The water layer was adjusted to pH 2.0 with 5% H3PO4 added, and extracted again with AcOEt. The AcOEt layer was washed with H2O and saturated aqueous NaCl solution, successively, and dried over Na2SO4, followed by distilling off the AcOEt under reduced pressure. The residue was treated with Et2O, thus yielding 114 mg (54%) of 7-[2-phenyl-(Z)-2-methoxyiminoacetamido]-2α-methyl-3-methoxyiminomethylceph-3-em-4-carboxylic acid as crystals.

Workup

  1. distillationAfter distilling off the CF3COOH under reduced pressure
  2. dissolutionthe residue was dissolved in AcOEt
  3. additionadded
  4. extractionextracted again with AcOEt
  5. washThe AcOEt layer was washed with H2O and saturated aqueous NaCl solution
  6. dry with materialsuccessively, and dried over Na2SO4
  7. distillationby distilling off the AcOEt under reduced pressure
  8. additionThe residue was treated with Et2O

Sources & evidence

ORD record
ord-3a753aa644b34769bf9017366dc0a238
Source dataset
uspto-grants-1984_07
Patent number
US04463172

Reaction notes

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