Trifluoroacetic acid → HCID 131713344, compound

HRID 905484Notes

Reaction equation

HRID 905484 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:51]=[C:52]([NH2:56])[S:53][C:54]=1[Cl:55])[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:51]=[C:52]([NH2:56])[S:53][C:54]=1[Cl:55])[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 131713341HCID 131713341, compound

Product 1

HCID 131713344HCID 131713344, compoundYield 46.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

Trifluoroacetic acid (6.4 ml) was added to a solution of benzhydryl 7-[2-(1-tert-butoxycarbonylethoxyimino)-2-(2-amino-5-chlorothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer) (1.6 g) in methylene chloride (3.0 ml) and anisole (1.6 ml) under ice-cooling, and the mixture was stirred at ambient temperature for 1.5 hours. To the reaction mixture was added diisopropyl ether (50 ml), and the precipitates were collected by filtration and added to a mixture of water and ethyl acetate. After adjusting to pH 7.5 with 10% aqueous sodium hydroxide, the separated aqueous layer was adjusted to pH 2.2 with 10% hydrochloric acid and then saturated with sodium chloride, followed by extraction with a mixture of ethyl acetate and tetrahydrofuran (1:1). The extract was washed with a saturated aqueous sodium chloride and then dried over magnesium sulfate. Removal of the solvent gave 7-[2-(1-carboxyethoxyimino)-2-(2-amino-5-chlorothiazol-4-yl)-acetamido]-3-vinyl-3-cephem-4-carboxylic acid (syn isomer) (0.52 g).

Workup

  1. temperaturecooling
  2. filtrationthe precipitates were collected by filtration
  3. additionadded to a mixture of water and ethyl acetate
  4. extractionsaturated with sodium chloride, followed by extraction with a mixture of ethyl acetate and tetrahydrofuran (1:1)
  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-795b31e98a68427bbad61d1aac9d56ac
Source dataset
uspto-grants-1983_12
Patent number
US04423213

Reaction notes

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