Trifluoroacetic acid → HCID 131713094, compound

HRID 1284655Notes

Reaction equation

HRID 1284655 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:43]1[N:44]=[C:45]([NH:48][CH:49]=[O:50])[S:46][CH:47]=1)[C:5]([NH:7][CH:8]1[C:41](=[O:42])[N:10]2[C:11]([C:25]([O:27]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:26])=[C:12]([CH2:15][S:16][C:17]3[N:21]([CH2:22][C:23]#[CH:24])[N:20]=[N:19][N:18]=3)[CH2:13][S:14][C@H:9]12)=[O:6].C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][O:2][N:3]=[C:4]([C:43]1[N:44]=[C:45]([NH:48][CH:49]=[O:50])[S:46][CH:47]=1)[C:5]([NH:7][CH:8]1[C:41](=[O:42])[N:10]2[C:11]([C:25]([OH:27])=[O:26])=[C:12]([CH2:15][S:16][C:17]3[N:21]([CH2:22][C:23]#[CH:24])[N:20]=[N:19][N:18]=3)[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 131713090benzhydryl 7-[2-methoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-[1-(2-propynyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylate

Product 1

HCID 131713094HCID 131713094, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of benzhydryl 7-[2-methoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-[1-(2-propynyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylate (syn isomer) (2.8 g) in methylene chloride (24 ml) were added anisole (2.8 g) and trifluoroacetic acid (7.5 g) with stirring under ice-cooling and then the resulting mixture was stirred for one hour and 15 minutes at room temperature. After the evaporation of the reaction mixture, to the residue were added water and ethyl acetate. The mixture was adjusted to pH 7.0 with a saturated aqueous solution of sodium carbonate. The aqueous layer was separated and washed with ethyl acetate (×2) and thereto were added ethyl acetate and tetrahydrofuran. The mixture was adjusted to pH 2.0 with 10% hydrochloric acid. The organic layer was separated, washed with water, dried over magnesium sulfate, treated with activated charcoal and evaporated. The residue was pulverized in isopropyl ether, collected by filtration, washed with isopropyl ether and dried to give 7-[2-methoxyimino-2-(2-formamidothiazol- 4-yl)acetamido]-3-[1-(2-propynyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (1.48 g).

Workup

  1. temperaturecooling
  2. stirringthe resulting mixture was stirred for one hour and 15 minutes at room temperature
  3. customAfter the evaporation of the reaction mixture
  4. additionto the residue were added water and ethyl acetate
  5. customThe aqueous layer was separated
  6. washwashed with ethyl acetate (×2)
  7. additionwere added ethyl acetate and tetrahydrofuran
  8. customThe organic layer was separated
  9. washwashed with water
  10. dry with materialdried over magnesium sulfate
  11. additiontreated with activated charcoal
  12. customevaporated
  13. filtrationcollected by filtration
  14. washwashed with isopropyl ether
  15. customdried

Sources & evidence

ORD record
ord-87bcdc3287f84b8ebd684d14913fcea1
Source dataset
uspto-grants-1986_01
Patent number
US04563450

Reaction notes

Loading…