Chloranil → (17beta)-3-oxo-N-[2-(trifluoromethyl)phenyl]androsta-4,6-diene-17-carboxamide

HRID 749052Notes

Reaction equation

HRID 749052 reaction equation
[O:1]=[C:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:21]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]([F:33])([F:32])[F:31])=[O:22])=[CH:3]1.C1(Cl)C(=O)C(Cl)=C(Cl)C(=O)C=1Cl>C(O)(C)(C)C>[O:1]=[C:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4]([CH:5]=[CH:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:21]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]([F:31])([F:32])[F:33])=[O:22])=[CH:3]1

Participants

4

Reactant 2

HCID 8371ChloranilHCID 68973195HCID 68973195, compound

Product 1

HCID 68976085(17beta)-3-oxo-N-[2-(trifluoromethyl)phenyl]androsta-4,6-diene-17-carboxamide

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of (17β)-3-oxo-N-[2-(trifluoromethyl)phenyl]androst-4-ene-17-carboxamide (2-1) (3.74 g, 8.14 mmol) and p-chloranil (2.40 g, 9.77 mmol) in t-butanol (40 mL) under N2 was heated to reflux for 90 min. The reaction was concentrated and the residue dissolved in EtOAc and washed with 0.5 N NaOH solution (2×60 mL), 10% KHSO4 solution, and brine. Upon removal of the solvent, the residue was purified by flash chromatography on silica gel (0 to 35% EtOAc-hexanes) to afford 5-2 as a brownish foam.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 90 min
  3. concentrationThe reaction was concentrated
  4. dissolutionthe residue dissolved in EtOAc
  5. washwashed with 0.5 N NaOH solution (2×60 mL), 10% KHSO4 solution, and brine
  6. customUpon removal of the solvent
  7. customthe residue was purified by flash chromatography on silica gel (0 to 35% EtOAc-hexanes)

Sources & evidence

ORD record
ord-96a7886f5da24bb397301b0e04231632
Source dataset
uspto-grants-2008_07
Patent number
US07402577B2

Reaction notes

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