Trifluoroacetic acid → HCID 131713210, compound

HRID 569424Notes

Reaction equation

HRID 569424 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1[S:13][N:12]=[C:11]([C:14](=[N:45][O:46][CH2:47][C:48]([O:50]C(C)(C)C)=[O:49])[C:15]([NH:17][CH:18]2[C:43](=[O:44])[N:20]3[C:21]([C:27]([O:29]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:28])=[C:22]([CH:25]=[CH2:26])[CH2:23][S:24][C@H:19]23)=[O:16])[N:10]=1.C(OC(C)C)(C)C>C(Cl)Cl.C1(OC)C=CC=CC=1>[NH2:8][C:9]1[S:13][N:12]=[C:11]([C:14](=[N:45][O:46][CH2:47][C:48]([OH:50])=[O:49])[C:15]([NH:17][CH:18]2[C:43](=[O:44])[N:20]3[C:21]([C:27]([OH:29])=[O:28])=[C:22]([CH:25]=[CH2:26])[CH2:23][S:24][C@H:19]23)=[O:16])[N:10]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 131713211HCID 131713211, compound

Product 1

HCID 131713210HCID 131713210, compoundYield 60.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

Trifluoroacetic acid (13.6 ml) was added to a solution of benzhydryl 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer) (3.4 g) in methylene chloride (7.0 ml) and anisole (3.4 ml) under ice-cooling, followed by stirring at ambient temperature for 1.5 hours. The reaction mixture was added dropwise to diisopropyl ether (150 ml), and the precipitates were collected by filtration and then added to a mixture of water and ethyl acetate. After adjusting to pH 7.5 with a saturated aqueous sodium bicarbonate, the aqueous layer was separated and then adjusted to pH 2.0 with 10% hydrochloric acid. The precipitates were collected by filtration, washed with cold water and then dried to obtain 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-carboxymethoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylic acid (syn isomer) (1.39 g).

Workup

  1. temperaturecooling
  2. filtrationthe precipitates were collected by filtration
  3. additionadded to a mixture of water and ethyl acetate
  4. customthe aqueous layer was separated
  5. filtrationThe precipitates were collected by filtration
  6. washwashed with cold water
  7. customdried

Sources & evidence

ORD record
ord-76b97bf5aeee41dc8ac22f8d529d2e04
Source dataset
uspto-grants-1988_03
Patent number
US04731443

Reaction notes

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