Trifluoroacetic acid → HCID 131713636, compound

HRID 358088Notes

Reaction equation

HRID 358088 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13]([CH2:15][O:16][N:17]=[C:18]([C:49]1[CH:53]=[N:52][S:51][N:50]=1)[C:19]([NH:21][CH:22]1[C:47](=[O:48])[N:24]2[C:25]([C:31]([O:33]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:32])=[C:26]([CH:29]=[CH2:30])[CH2:27][S:28][C@H:23]12)=[O:20])=[O:14])(C)(C)C.C(OC(C)C)(C)C>C(Cl)Cl.C1(OC)C=CC=CC=1>[C:13]([CH2:15][O:16][N:17]=[C:18]([C:49]1[CH:53]=[N:52][S:51][N:50]=1)[C:19]([NH:21][CH:22]1[C:47](=[O:48])[N:24]2[C:25]([C:31]([OH:33])=[O:32])=[C:26]([CH:29]=[CH2:30])[CH2:27][S:28][C@H:23]12)=[O:20])([OH:14])=[O:12]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 131713637HCID 131713637, compound

Product 1

HCID 131713636HCID 131713636, compoundYield 49.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

Trifluoroacetic acid (6.75 ml) was added to a solution of benzhydryl 7-[2-tert-butoxycarbonylmethoxyimino-2-(1,2,5-thiadiazol-3-yl)acetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer) (2.9 g) in methylene chloride (5.8 ml) and anisole (1.9 ml) under ice-cooling, and the mixture was stirred for 4 hours at ambient temperature. The resultant solution was added dropwise to diisopropyl ether (100 ml) and the precipitates were collected by filtration. The precipitates were added to a mixture of water and ethyl acetate and adjusted to pH 7.0 with 10% aqueous sodium hydroxide. The separated aqueous layer was adjusted to pH 2 with 10% hydrochloric acid and extracted with ethyl acetate. The extract was washed with an aqueous sodium chloride and then dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with diisopropyl ether and collected by filtration to give 7-[2-carboxymethoxyimino-2-(1,2,5-thiadiazol-3-yl)acetamido]-3-vinyl-3-cephem-4-carboxylic acid (syn isomer) (0.96 g).

Workup

  1. temperaturecooling
  2. filtrationthe precipitates were collected by filtration
  3. additionThe precipitates were added to a mixture of water and ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with an aqueous sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was triturated with diisopropyl ether
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-1fc52152010c43d19a8b75291aabd8e1
Source dataset
uspto-grants-1984_08
Patent number
US04464369

Reaction notes

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