Trifluoroacetic acid → HCID 131713338, compound

HRID 1154255Notes

Reaction equation

HRID 1154255 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13]([CH:15]([O:17][N:18]=[C:19]([C:50]1[N:54]=[C:53]([NH2:55])[S:52][N:51]=1)[C:20]([NH:22][CH:23]1[C:48](=[O:49])[N:25]2[C:26]([C:32]([O:34]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:33])=[C:27]([CH:30]=[CH2:31])[CH2:28][S:29][C@H:24]12)=[O:21])[CH3:16])=[O:14])(C)(C)C.C(OC(C)C)(C)C>C(Cl)Cl.C1(OC)C=CC=CC=1>[C:13]([CH:15]([O:17][N:18]=[C:19]([C:50]1[N:54]=[C:53]([NH2:55])[S:52][N:51]=1)[C:20]([NH:22][CH:23]1[C:48](=[O:49])[N:25]2[C:26]([C:32]([OH:34])=[O:33])=[C:27]([CH:30]=[CH2:31])[CH2:28][S:29][C@H:24]12)=[O:21])[CH3:16])([OH:14])=[O:12]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 131713339HCID 131713339, compound

Product 1

HCID 131713338HCID 131713338, compoundYield 33.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

Trifluoroacetic acid (9.6 ml) was added to a solution of benzhydryl 7-[2-(1-tert-butoxycarbonylethoxyimino)-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer) (2.4 g) in methylene chloride (5 ml) and anisole (2.4 ml) under ice-cooling, and the mixture was stirred for 1 hour at room 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 then adjusted to pH 7.5 with 10% aqueous sodium hydroxide. The separated aqueous layer was saturated with sodium chloride and adjusted to pH 1.5 with 10% hydrochloric acid, followed by extraction with a mixed solvent of ethyl acetate and tetrahydrofuran (1:1 by volume). The extract was washed with a saturated aqueous sodium chloride and dried over magnesium sulfate. Removal of the solvent gave 7-[2-(1-carboxyethoxyimino)-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-vinyl-3-cephem-4-carboxylic acid (syn isomer) (0.55 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. extractionfollowed by extraction with a mixed solvent of ethyl acetate and tetrahydrofuran (1:1 by volume)
  5. washThe extract was washed with a saturated aqueous sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-b9ed18a23599446dbb11acac01fb569a
Source dataset
uspto-grants-1984_12
Patent number
US04487927

Reaction notes

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