HCID 70146254, compound → HCID 11034899, compound

HRID 840183Notes

Reaction equation

HRID 840183 reaction equation
C([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][C@@H:13](Br)[C:14]32[O:27][CH2:26][CH2:25][O:24]3)[CH2:6]1)(=O)C>CS(C)=O>[CH2:26]1[CH2:25][O:24][C:14]2([CH:13]=[CH:12][C@H:11]3[C@H:10]4[C@H:19]([CH2:18][CH2:17][C@:15]23[CH3:16])[C@:20]2([CH3:23])[C:7]([CH2:6][C@@H:5]([OH:4])[CH2:22][CH2:21]2)=[CH:8][CH2:9]4)[O:27]1

Participants

3

Reactant 1

HCID 70146254HCID 70146254, compound

Product 1

HCID 11034899HCID 11034899, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
45 °C

Procedure

16α-Bromo-17,17-ethylenedioxy-androst-5-en-3β-ol 3-acetate from Example 28A (50.000 g, 110.28 mmol) is dissolved in dimethyl sulfoxide (DMSO; 500 mL) and the solution is warmed to 45° C. under an inert atmosphere. After 22 hours, the reaction is partitioned between ether (2000 mL) and water (750 mL). The layers are separated and the ether solution is washed with brine (2×500 mL), dried over MgSO4, filtered and evaporated to dryness. The residue is recrystallized from ethanol-water to afford the title compound.

Workup

  1. customthe reaction is partitioned between ether (2000 mL) and water (750 mL)
  2. customThe layers are separated
  3. washthe ether solution is washed with brine (2×500 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue is recrystallized from ethanol-water

Sources & evidence

ORD record
ord-4e3d6d0e6cac42a39df120960bf3ba15
Source dataset
uspto-grants-2002_04
Patent number
US06365597B1

Reaction notes

Loading…