Trifluoroacetic acid → HCID 131713616, compound

HRID 1463103Notes

Reaction equation

HRID 1463103 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[N:37][O:38][CH2:39][C:40]([O:42]C(C)(C)C)=[O:41])[C:15]([NH:17][CH:18]2[C:35](=[O:36])[N:20]3[C:21]([C:28]([O:30]C(C)(C)C)=[O:29])=[C:22]([CH2:25][O:26][CH3:27])[CH2:23][S:24][C@H:19]23)=[O:16])[N:13]=1.C(OC(C)C)(C)C>C(Cl)Cl.C1(OC)C=CC=CC=1>[NH2:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[N:37][O:38][CH2:39][C:40]([OH:42])=[O:41])[C:15]([NH:17][CH:18]2[C:35](=[O:36])[N:20]3[C:21]([C:28]([OH:30])=[O:29])=[C:22]([CH2:25][O:26][CH3:27])[CH2:23][S:24][C@H:19]23)=[O:16])[N:13]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 131713614HCID 131713614, compound

Product 1

HCID 131713616HCID 131713616, compoundYield 67.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

Trifluoroacetic acid (8.4 ml) was added to a solution of tert-butyl 7-[2-(2-aminothiazol-4-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-methoxymethyl-3-cephem-4-carboxylate (syn isomer) (2.1 g) in methylene chloride (4.2 ml) and anisole (2.1 ml) under ice-cooling, and the mixture was stirred at ambient temperature for 1.5 hours. The resultant solution was added dropwise to diisopropyl ether (100 ml) and the precipitated substance was collected by filtration. This substance was added to a mixture of water and ethyl acetate, followed by adjusting to pH 7.5 with 10% aqueous sodium hydroxide. The separated aqueous layer was saturated with sodium chloride and then adjusted to pH 1.5 with 10% hydrochloric acid. After extraction with a mixture of ethyl acetate and tetrahydrofuran (1:1 by volume), the extract was washed with a saturated aqueous sodium chloride, dried over magnesium sulfate and then evaporated. The residue was washed with diethyl ether and collected by filtration to give 7-[2-(2-aminothiazol-4-yl)-2-carboxymethoxyiminoacetamido]-3-methoxymethyl-3-cephem-4-carboxylic acid (syn isomer) (1.14 g).

Workup

  1. temperaturecooling
  2. filtrationthe precipitated substance was collected by filtration
  3. additionThis substance was added to a mixture of water and ethyl acetate
  4. extractionAfter extraction
  5. additionwith a mixture of ethyl acetate and tetrahydrofuran (1:1 by volume)
  6. washthe extract was washed with a saturated aqueous sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. washThe residue was washed with diethyl ether
  10. filtrationcollected by filtration

Sources & evidence

ORD record
ord-2a1aadc2a023490d87ee6ef5a1ce659f
Source dataset
uspto-grants-1984_07
Patent number
US04462999

Reaction notes

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