Trifluoroacetic acid → HCID 178481649, compound

HRID 34497Notes

Reaction equation

HRID 34497 reaction equation
C([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:66][O:67][CH:68]([F:70])[F:69])[C:27]([NH:29][CH:30]2[C:64](=[O:65])[N:32]3[C:33]([C:48]([O:50]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:49])=[C:34]([CH2:37][S:38][C:39]4[N:44]([CH3:45])[C:43](=[O:46])[C:42]([OH:47])=[N:41][N:40]=4)[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(OC(C)C)(C)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[NH2:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:66][O:67][CH:68]([F:69])[F:70])[C:27]([NH:29][CH:30]2[C:64](=[O:65])[N:32]3[C:33]([C:48]([OH:50])=[O:49])=[C:34]([CH2:37][S:38][C:39]4[N:44]([CH3:45])[C:43](=[O:46])[C:42]([OH:47])=[N:41][N:40]=4)[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 7914Diisopropyl EtherHCID 516892Sodium BicarbonateHCID 178481648HCID 178481648, compound

Product 1

HCID 178481649HCID 178481649, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of benzhydryl 7-[2-(2-tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-(4-methyl-5-oxo-6-hydroxy-4,5-dihydro-1,2,4-triazin-3-yl)thiomethyl-3-cephem-4-carboxylate (syn isomer) (1.20 g) and anisole (2.5 ml) in methylene chloride (2.5 ml) was added trifluoroacetic acid (5 ml) under ice-cooling. After being stirred for 30 minutes, the mixture was poured into diisopropyl ether (50 ml). The resultant mixture was adjusted to pH 7 with an aqueous solution of sodium bicarbonate. The separated aqueous layer was washed with ethyl acetate, acidified with 6N hydrochloric acid and extracted with a mixture of tetrahydrofuran and ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried and evaporated under reduced pressure. The residue was triturated in diethyl ether and collected by filtration to give 7-[2-(2-aminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-(4-methyl-5-oxo-6-hydroxy-4,5-dihydro-1,2,4-triazin-3-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (600 mg).

Workup

  1. temperaturecooling
  2. washThe separated aqueous layer was washed with ethyl acetate
  3. extractionextracted with a mixture of tetrahydrofuran and ethyl acetate
  4. washThe extract was washed with a saturated aqueous solution of sodium chloride
  5. customdried
  6. customevaporated under reduced pressure
  7. customThe residue was triturated in diethyl ether
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-1b11f740150d4069855dec58ac63b00e
Source dataset
uspto-grants-1988_08
Patent number
US04761410

Reaction notes

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