Anisole → HCID 178436974, compound

HRID 1262772Notes

Reaction equation

HRID 1262772 reaction equation
[C:1]1([C:7](=[N:38][O:39][CH2:40][C:41]([O:43]C(C)(C)C)=[O:42])[C:8]([NH:10][CH:11]2[C:36](=[O:37])[N:13]3[C:14]([C:20]([O:22]C(C4C=CC=CC=4)C4C=CC=CC=4)=[S:21])=[C:15]([CH2:18][CH3:19])[CH2:16][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>FC(F)(F)C(O)=O>[C:1]1([C:7](=[N:38][O:39][CH2:40][C:41]([OH:43])=[O:42])[C:8]([NH:10][CH:11]2[C:36](=[O:37])[N:13]3[C:14]([C:20]([OH:22])=[S:21])=[C:15]([CH2:18][CH3:19])[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 7519AnisoleHCID 131713554HCID 131713554, compound

Product 1

HCID 178436974HCID 178436974, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The solution of benzhydryl 7-[2-phenyl-2-tertbutoxycarbonylmethoxyiminoacetamido]-3-ethylthio-3-cephem-4-carboxylate (syn isomer, 2.0 g) and anisole (2.0 ml) in trifluoroacetic acid (8 ml) was stirred for 90 minutes at ambient temperature. The resultant solution was evaporated under reduced pressure and the residual oil was dissolved in an aqueous solution of sodium bicarbonate. After the solution was washed with ethyl acetate, the solution was adjusted to pH 2.0 with 10% hydrochloric acid and extracted with ethyl acetate (100 ml). The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give 7-[2-phenyl-2-carboxymethoxyiminoacetamido]-3-ethylthio-3-cephem-4-carboxylic acid (syn isomer, 1.3 g), mp. 103° to 107° C. (dec.).

Workup

  1. customThe resultant solution was evaporated under reduced pressure
  2. dissolutionthe residual oil was dissolved in an aqueous solution of sodium bicarbonate
  3. washAfter the solution was washed with ethyl acetate
  4. extractionextracted with ethyl acetate (100 ml)
  5. washThe extract was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-650a58fae65a407dbbeb13470d4a6333
Source dataset
uspto-grants-1984_06
Patent number
US04452851

Reaction notes

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