HCID 10581365, compound → HCID 10594394, compound

HRID 356989Notes

Reaction equation

HRID 356989 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:29]([F:53])[C@H:8]2[O:9]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[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:29]([F:53])[C@H:8]2[OH:9])[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 10581365HCID 10581365, compound

Product 1

HCID 10594394HCID 10594394, compoundYield 74.7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Compound 5 (0.28 g, 0.32 mmol) was dissolved in 10% CF3COOH in CHCl3 (20 mL) and stirred at room temperature in a stoppered flask for 45 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, evaporated to dryness and crystallized from MeOH/H2O to give 85 mg (74%) of compound 7 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. customevaporated to dryness
  4. customcrystallized from MeOH/H2O

Sources & evidence

ORD record
ord-d2d193ded0e54e7a844522e0d725540f
Source dataset
uspto-grants-1998_11
Patent number
US05840743

Reaction notes

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