Trifluoroacetic acid → HCID 67859710, compound

HRID 647740Notes

Reaction equation

HRID 647740 reaction equation
C([NH:20][C:21]1[S:25][C:24]([CH2:26][C:27]([NH:29][CH:30]2[C:55](=[O:56])[N:32]3[C:33]([C:39]([O:41]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:40])=[C:34]([CH:37]=[CH2:38])[CH2:35][S:36][C@H:31]23)=[O:28])=[N:23][N:22]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(OC(C)C)(C)C>C(Cl)Cl>[NH2:20][C:21]1[S:25][C:24]([CH2:26][C:27]([NH:29][CH:30]2[C:55](=[O:56])[N:32]3[C:33]([C:39]([OH:41])=[O:40])=[C:34]([CH:37]=[CH2:38])[CH2:35][S:36][C@H:31]23)=[O:28])=[N:23][N:22]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 7914Diisopropyl EtherHCID 67859952HCID 67859952, compound

Product 1

HCID 67859710HCID 67859710, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of benzhydryl 7-[2-(5-tritylamino-1,3,4-thiadiazol-2-yl)acetamido]-3-vinyl-3-cephem-4-carboxylate (2.6 g) in methylene chloride (30 ml) and anisole (2.1 g) was added trifluoroacetic acid (7.6 g) under ice-cooling, followed by stirring at ambient temperature for 1.5 hours. The reaction mixture was poured into diisopropyl ether (300 ml), and the precipitates were collected by filtration and suspended in water (40 ml). After adjusting to pH 7 with 10% aqueous sodium hydroxide, the aqueous solution was washed with ethyl acetate and then adjusted to pH 5 with 10% hydrochloric acid. The organic solvent included in the resultant aqueous solution was completely removed by evaporation, and the resultant aqueous solution was adjusted to pH 4 with dilute acetic acid, which was chromatographed on a non-ionic adsorption resin "Diaion HP-20" (50 ml). After washing with water, elution was carried out with 30% isopropyl alcohol, and the fractions containing a desired compound were collected and then concentrated under reduced pressure. The concentrate was lyophilized to obtain 7-[2-(5-amino-1,3,4-thiadiazol-2-yl)-acetamido]-3-vinyl-3-cephem-4-carboxylic acid (0.31 g).

Workup

  1. temperaturecooling
  2. filtrationthe precipitates were collected by filtration
  3. washthe aqueous solution was washed with ethyl acetate
  4. customwas completely removed by evaporation
  5. customwas chromatographed on a non-ionic adsorption resin "Diaion HP-20" (50 ml)
  6. washAfter washing with water, elution
  7. additionthe fractions containing a desired compound
  8. customwere collected
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9d2fa8544c9f47748b0b48f9822173cd
Source dataset
uspto-grants-1983_10
Patent number
US04409214

Reaction notes

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