HCID 10676977, compound → HCID 9885007, compound

HRID 356988Notes

Reaction equation

HRID 356988 reaction equation
[Cl:1][C:2]1[N:6]([C@@H:7]2[O:31][C@H:30]([CH2:32][O:33]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C@@H:9]([O:10]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C@@H:8]2[F:53])[C:5]2[CH:54]=[C:55]([Cl:59])[C:56]([Cl:58])=[CH:57][C:4]=2[N:3]=1>C(O)(C(F)(F)F)=O.C(Cl)(Cl)Cl>[Cl:1][C:2]1[N:6]([C@@H:7]2[O:31][C@H:30]([CH2:32][OH:33])[C@@H:9]([OH:10])[C@@H:8]2[F:53])[C:5]2[CH:54]=[C:55]([Cl:59])[C:56]([Cl:58])=[CH:57][C:4]=2[N:3]=1

Participants

4

Reactant 1

HCID 10676977HCID 10676977, compound

Product 1

HCID 9885007HCID 9885007, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Compound 4 (0.10 g, 0.12 mmol) was dissolved in 10% CF3COOH in CHCl3 (10 mL) and stirred at room temperature in a stoppered flask for 60 min. The reaction mixture was evaporated to dryness in vacuo, the oily residue was purified by flash chromatography (EtOAc/hexane 5:1, 2 cm×15 cm), appropriate fractions pooled, solvent removed in vacuo and the white residue crystallized from MeOH/H2O to give 25 mg (60%) of compound 6 as white crystals.

Workup

  1. customThe reaction mixture was evaporated to dryness in vacuo
  2. customthe oily residue was purified by flash chromatography (EtOAc/hexane 5:1, 2 cm×15 cm), appropriate fractions
  3. customsolvent removed in vacuo
  4. customthe white residue crystallized from MeOH/H2O

Sources & evidence

ORD record
ord-93c7eaede5074e09a67d1dbbc2e31117
Source dataset
uspto-grants-1998_11
Patent number
US05840743

Reaction notes

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