p-Toluenesulfonic acid → HCID 18604267, compound

HRID 1111143Notes

Reaction equation

HRID 1111143 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4](S(O)(=O)=O)=[CH:3][CH:2]=1.[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1.[CH2:18](N(CC)CC)[CH3:19].O1[CH2:29][CH2:28][CH2:27][CH2:26]1>C(OCC)(=O)C>[CH3:26][C@:27]12[CH2:19][CH2:18][C:5]3[C@@H:6]([CH2:13][CH2:14][C:15]4[C:4]=3[CH2:3][CH2:2][C:17](=[O:12])[CH:16]=4)[C@@H:1]1[CH2:11][CH2:29][CH2:28]2

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8028TetrahydrofuranHCID 80803,4-dihydro-2H-pyranHCID 8471Triethylamine

Product 1

HCID 18604267HCID 18604267, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

570 mg of p-toluene sulfonic acid were added to a solution of 1.075 g of 11β-(4-dimethylaminophenyl -17α-(prop-1-ynyl)-Δ4,9 -estradiene-17β-ol-3-one [prepared Example 1 of EPC Application Ser. No. 57,115] in 10 ml of tetrahydrofuran and 2 ml of 3,4-dihydro-pyran and the mixture was stirred at room temperature for one hour. 1 ml of triethylamine was added to the mixture which was then diluted with ethyl acetate. The organic phase was washed with aqueous saturated sodium bicabonate solution, dried and evaporated to dryness under reduced pressure to obtain 2 g of raw 11β-(4-dimethylaminophenyl)-17α-(prop-1-ynyl)17β-2RS-tetrahydropyranyloxy)-66 4,9 -estradiene 3-one in the form of a yellow oil.

Workup

  1. customprepared Example 1 of EPC Application Ser
  2. washThe organic phase was washed with aqueous saturated sodium bicabonate solution
  3. customdried
  4. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-6113caa372bd4b8b8b8da1466b19180f
Source dataset
uspto-grants-1990_12
Patent number
US04978657

Reaction notes

Loading…