Ethyl Acetate → HCID 69626993, compound

HRID 650339Notes

Reaction equation

HRID 650339 reaction equation
C(O[C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:20]([CH2:21][CH2:22][C@:6]12[CH3:7])[C:19]1[CH:18]=[CH:17][C:16](OC2CCCCO2)=[CH:15][C:14]=1[CH2:13][C@H:12]3CCCCCNC)(=O)C.[H-].[Na+].Cl[CH2:40]CCC(SC(CCCCl)CCC(F)(F)C(F)(F)F)CCC(F)(F)C(F)(F)F.[C:68]([O:71][CH2:72][CH3:73])(=[O:70])[CH3:69]>CN(C=O)C>[O:71]1[CH2:72][CH2:73][CH2:40][CH2:69][CH:68]1[O:70][CH2:7][C@:6]12[CH2:22][CH2:21][C@H:20]3[C@@H:11]([CH2:12][CH2:13][C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=43)[C@@H:8]1[CH2:9][CH2:10][CH2:5]2

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 22941792HCID 22941792, compoundHCID 86696804HCID 86696804, compound

Product 1

HCID 69626993HCID 69626993, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of 1.64 g of 17β-acetoxy-7α-(5-methylaminopentyl)-3-(tetrahydropyran-2-yloxy)-estra-1,3,5(10)-triene in 25 ml of absolute DMF is stirred with 159 mg of 80% sodium hydride under nitrogen for 2 hours at room temperature. 1.43 g of 3-chloro-propyl4,4,5,5,5-pentafluoropentylsulfide in 7 ml of absolute DMF is then added in drops and then stirred for 22 more hours at 80° C. The reaction solution is then diluted with ethyl acetate, washed with water, dried, concentrated by evaporation, and the residue is chromatographed on silica gel. 820 mg of 17β-acetoxy-7α-{5-[N-methyl-N-3-(4,4,5,5,5-pentafluoropentylthio)-propylamino]-pentyl}-3-(tetrahydropyran-2-yloxy-estra-1,3,5(10)-triene is obtained as oil.

Workup

  1. washwashed with water
  2. customdried
  3. concentrationconcentrated by evaporation
  4. customthe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-ef43f6c6958549aa80d9b4cb1198e99f
Source dataset
uspto-grants-2001_08
Patent number
US06271403B1

Reaction notes

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