Water → HCID 15870676, compound

HRID 1838885Notes

Reaction equation

HRID 1838885 reaction equation
[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C:4]1[CH:5]=[CH:6][C:7]([O:37][CH:38]3[CH2:43][CH2:42][CH2:41][CH2:40][O:39]3)=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]OS(C1C=CC(C)=CC=1)(=O)=O.[CH3:44][NH:45][CH2:46][CH2:47][CH2:48][S:49][CH2:50][CH2:51][CH2:52][C:53]([F:59])([F:58])[C:54]([F:57])([F:56])[F:55].O>CN(C=O)C>[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C:4]1[CH:9]=[CH:8][C:7]([O:37][CH:38]3[CH2:43][CH2:42][CH2:41][CH2:40][O:39]3)=[CH:6][C:5]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:45]([CH3:44])[CH2:46][CH2:47][CH2:48][S:49][CH2:50][CH2:51][CH2:52][C:53]([F:59])([F:58])[C:54]([F:55])([F:56])[F:57]

Participants

5

Reactant 3

HCID 962WaterHCID 11391445HCID 11391445, compoundHCID 22941779HCID 22941779, compound

Product 1

HCID 15870676HCID 15870676, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.0 g of 11β-fluoro-3-(tetrahydropyran-2-yloxy)-7α-(5-p-toluenesulphonyloxypentyl)oestra-1,3,5(10)-trien-17-one in 44 ml of DMF are stirred at 80° C. with 1.2 g of methyl-[3-(4,4,5,5,5-pentafluoropentylthio)propyl]-amine. After 6.5 h, the reaction mixture is treated with water. The mixture is extracted with ethyl acetate, washed with saturated sodium chloride solution and concentrated in vacuo. After chromatographing the crude product on silica gel using a methylene chloride-methanol gradient, 1.3 g of 11-fluoro-7α-{5-[N-methyl-N-3-(4,4,5,5,5-pentafluoropentylthio)propylamino]-pentyl}-3-(tetrahydropyran-2-yloxy)oestra-1,3,5(10)-trien-17-one are obtained as an oil.

Workup

  1. extractionThe mixture is extracted with ethyl acetate
  2. washwashed with saturated sodium chloride solution
  3. concentrationconcentrated in vacuo
  4. customare obtained as an oil

Sources & evidence

ORD record
ord-24ac6fbd6c804e4e87ec259a932154cf
Source dataset
uspto-grants-2004_01
Patent number
US06677324B1

Reaction notes

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