Trifluoroacetic acid → 7-[2-(2-Methanesulfonamidothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylic acid

HRID 1154220Notes

Reaction equation

HRID 1154220 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[S:7][CH:8]=[C:9]([CH2:11][C:12]([NH:14][CH:15]2[C:40](=[O:41])[N:17]3[C:18]([C:24]([O:26]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:25])=[C:19]([CH:22]=[CH2:23])[CH2:20][S:21][C@H:16]23)=[O:13])[N:10]=1)(=[O:4])=[O:3].C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][S:2]([NH:5][C:6]1[S:7][CH:8]=[C:9]([CH2:11][C:12]([NH:14][CH:15]2[C:40](=[O:41])[N:17]3[C:18]([C:24]([OH:26])=[O:25])=[C:19]([CH:22]=[CH2:23])[CH2:20][S:21][C@H:16]23)=[O:13])[N:10]=1)(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 88469469Benzhydryl 7-[2-(2-methanesulfonamidothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylate

Product 1

HCID 884694507-[2-(2-Methanesulfonamidothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylic acidYield 45.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of benzhydryl 7-[2-(2-methanesulfonamidothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylate (4.5 g) in methylene chloride (30 ml) and anisole (4.6 g) was added 2,2,2-trifluoroacetic acid (16.8 g) under ice-cooling, and the solution was stirred at ambient temperature for an hour. After evaporation of the reaction mixture, thereto were added water and ethyl acetate, followed by adjusting to pH 7 with 1N aqueous solution of sodium hydroxide. To the separated aqueous layer were added ethyl acetate and tetrahydrofuran, followed by adjusting to pH 2 with 10% hydrochloric acid. After the organic layer was separated out, it was washed with an aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. Removal of the solvent gave a residue, which was washed with diethyl ether to obtain 7-[2-(2-methanesulfonamidothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylic acid (1.5 g).

Workup

  1. temperaturecooling
  2. customAfter evaporation of the reaction mixture
  3. additionwere added water and ethyl acetate
  4. additionTo the separated aqueous layer were added ethyl acetate and tetrahydrofuran
  5. customAfter the organic layer was separated out
  6. washit was washed with an aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customRemoval of the solvent
  9. customgave a residue, which
  10. washwas washed with diethyl ether

Sources & evidence

ORD record
ord-139b63135e124c8197618c4b87ece9d9
Source dataset
uspto-grants-1984_12
Patent number
US04487927

Reaction notes

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