Trifluoroacetic acid → HCID 141560927, compound

HRID 1591270Notes

Reaction equation

HRID 1591270 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:43]/[O:44][CH3:45])/[C:8]([NH:10][CH:11]2[C:41](=[O:42])[N:13]3[C:14]([C:25]([O:27]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:26])=[C:15]([C:18]4[C:21](=[O:22])[C:20](=[O:23])[C:19]=4[NH2:24])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>P([O-])([O-])([O-])=O.[NH4+].[NH4+].[NH4+]>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:43]/[O:44][CH3:45])/[C:8]([NH:10][CH:11]2[C:41](=[O:42])[N:13]3[C:14]([C:25]([OH:27])=[O:26])=[C:15]([C:18]4[C:21](=[O:22])[C:20](=[O:23])[C:19]=4[NH2:24])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 141560930HCID 141560930, compound

Product 1

HCID 141560927HCID 141560927, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 159282Ammonium phosphate, tribasicSolvent

Procedure

Diphenylmethyl 7-[2-(2-aminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-3-(2-amino-3,4-dioxo-1-cyclobutenyl)-3-cephem-4-carboxylate (400 mg) was added to a stirred, cooled (ice/H2O bath) solution of trifluoroacetic acid (6 mL) and anisole (0.5 mL). The cooling bath was removed and the solution stirred for 0.33 hr at ambient temperatures. The solution was concentrated and the residue macerated with methylene chloride to afford a yellow solid. The solid was dissolved in 0.05M (pH 6.5) ammonium phosphate. The solution was applied to a Michel-Miller HPLPLC column (22×300 mm) containing Partisil Prep 40 ODS-3. The column was eluted with 0.05M (pH 6.5) ammonium phosphate/acetonitrile (90:10). The appropriate fractions were combined and the pH lowered to 3.7 with the addition of dilute hydrochloric acid. The solution was concentrated to a volume of 50 mL when the title compound crystallized (155 mg, 52% yield).

Workup

  1. customThe cooling bath was removed
  2. concentrationThe solution was concentrated
  3. customthe residue macerated with methylene chloride to afford a yellow solid
  4. additioncontaining Partisil Prep 40 ODS-3
  5. washThe column was eluted with 0.05M (pH 6.5) ammonium phosphate/acetonitrile (90:10)
  6. additionthe pH lowered to 3.7 with the addition of dilute hydrochloric acid
  7. concentrationThe solution was concentrated to a volume of 50 mL when the title compound
  8. customcrystallized (155 mg, 52% yield)

Sources & evidence

ORD record
ord-abfe16bfb3904c59aad1e2de0791da9a
Source dataset
uspto-grants-1993_04
Patent number
US05206360

Reaction notes

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