Trifluoroacetic acid → HCID 178480522, compound

HRID 1614083Notes

Reaction equation

HRID 1614083 reaction equation
[Cl-].[NH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8](=[N:46][O:47]C2CCC=C2)[C:9]([NH:11][C@@H:12]2[C:44](=[O:45])[N:14]3[C:15]([C:28]([O:30]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:29])=[C:16]([CH2:19][N+:20]4[N:21]([CH3:27])[CH:22]=[C:23]([CH2:25][OH:26])[CH:24]=4)[CH2:17][S:18][C@H:13]23)=[O:10])[N:7]=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>O.C(Cl)Cl>[NH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8](=[N:46][OH:47])[C:9]([NH:11][C@@H:12]2[C:44](=[O:45])[N:14]3[C:15]([C:28]([O-:30])=[O:29])=[C:16]([CH2:19][N+:20]4[N:21]([CH3:27])[CH:22]=[C:23]([CH2:25][OH:26])[CH:24]=4)[CH2:17][S:18][C@H:13]23)=[O:10])[N:7]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 516892Sodium BicarbonateHCID 178480521HCID 178480521, compound

Product 1

HCID 178480522HCID 178480522, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of benzhydryl 7β-[2-(2-aminothiazol-4-yl)-2-(2-cyclopenten-1-yloxyimino)acetamido]-3-(4-hydroxymethyl-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate chloride (syn isomer, 1.9 g), anisole (2 ml) and methylene chloride (6 ml) was added trifluoroacetic acid (4 ml) under ice-cooling with stirring. After stirring at the same temperature for 1 hour, the mixture was dissolved in water and the solution was adjusted to pH 4 with 5% aqueous solution of sodium bicarbonate. The solution was subjected to column chromatography on macroporous non-ionic adsorption resin "Diaion HP-20" and eluted with 3% aqueous solution of isopropyl alcohol. The fractions containing the object compound were collected, combined, concentrated, and finally lyophilized to give 7β-[2-(2-aminothiazol-4-yl)-2-(hydroxyimino)acetamido]-3-(4-hydroxymethyl-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate (syn isomer, 0.32 g).

Workup

  1. temperaturecooling
  2. stirringAfter stirring at the same temperature for 1 hour
  3. washeluted with 3% aqueous solution of isopropyl alcohol
  4. additionThe fractions containing the object compound
  5. customwere collected
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ce0a2f2ac31e451fbc61f54d58125ee4
Source dataset
uspto-grants-1993_03
Patent number
US05194432

Reaction notes

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