HCID 68972999, compound → HCID 68973002, compound

HRID 749050Notes

Reaction equation

HRID 749050 reaction equation
O[CH2:2][CH:3]1[C:20]2[C@:15]([CH3:22])([CH2:16][CH2:17][C:18](=[O:21])[CH:19]=2)[C@@H:14]2[C@H:5]([C@H:6]3[C@@:10]([CH2:12][CH2:13]2)([CH3:11])[C@@H:9]([C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=2)=[O:24])[CH2:8][CH2:7]3)[CH2:4]1>Cl.O1CCOCC1>[CH2:2]=[C:3]1[C:20]2[C@:15]([CH3:22])([CH2:16][CH2:17][C:18](=[O:21])[CH:19]=2)[C@@H:14]2[C@H:5]([C@H:6]3[C@@:10]([CH2:12][CH2:13]2)([CH3:11])[C@@H:9]([C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:33])([F:35])[F:34])=[CH:28][CH:27]=2)=[O:24])[CH2:8][CH2:7]3)[CH2:4]1

Participants

4

Reactant 1

HCID 68972999HCID 68972999, compound

Product 1

HCID 68973002HCID 68973002, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of (17β)-6-(hydroxymethyl)-3-oxo-N-[4-(trifluoromethyl)phenyl]androst-4-ene-17-carboxamide (3-2 and 3-3) (0.57 g, 1.2 mmol) was dissolved in 15 mL 0.6N HCl in dioxane and stirred at rt. After 3 hr, it was diluted with a large excess of dioxane and stirred overnight. After removal of the solvent, the residue was dissolved in CHCl3 and washed with water, saturated NaHCO3 solution, and brine, then dried with MgSO4 and concentrated. The residue was purified by flash silica gel chromatography (0 to 50% EtOAc/hexane) to afford 3-4 as the desired product.

Workup

  1. stirringstirred overnight
  2. customAfter removal of the solvent
  3. dissolutionthe residue was dissolved in CHCl3
  4. washwashed with water, saturated NaHCO3 solution, and brine
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash silica gel chromatography (0 to 50% EtOAc/hexane)

Sources & evidence

ORD record
ord-cc43d94bcfaf4748a6a1d0e55a7fd4b2
Source dataset
uspto-grants-2008_07
Patent number
US07402577B2

Reaction notes

Loading…