Water → HCID 15858644, compound

HRID 1838892Notes

Reaction equation

HRID 1838892 reaction equation
[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C@@H:16]2O)[C@H:12]2[C@H:3]1[C:4]1[CH:5]=[CH:6][C:7]([OH:28])=[CH:8][C:9]=1[CH2:10][CH:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][CH3:27].S(C1C=CC(C)=CC=1)(O[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][C:40]([F:46])([F:45])[C:41]([F:44])([F:43])[F:42])(=O)=O.[OH2:54]>CN(C)C=O>[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C@@H:16]2[OH:54])[C@H:12]2[C@H:3]1[C:4]1[CH:5]=[CH:6][C:7]([OH:28])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([CH3:27])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][C:40]([F:45])([F:46])[C:41]([F:42])([F:43])[F:44]

Participants

5

Reactant 3

HCID 962WaterHCID 15858643HCID 15858643, compoundHCID 69935314HCID 69935314, compound

Product 1

HCID 15858644HCID 15858644, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.77 g of 11β-fluoro-7x-[5-(methylamino)-pentyl]oestra-1,3,5(10)-triene-3,17β-diol in 18 ml of dimethylformamide is stirred at a bath temperature of 80° C. for 1 hour with 1.4 g of 8,8,9,9,9-penta-fluorononyl tosylate. The mixture is then added to water, extracted 3 times with ethyl acetate, washed with water and sodium chloride solution, dried over sodium sulphate, concentrated in vacuo and the residue is chromatographed on silica gel using dichloromethane/methanol. 11β-Fluoro-7α-{5-[methyl(8,8,9,9,9-penta-fluorononyl)amino]pentyl}oestra-1,3,5(10)-triene-3,17β-diol is obtained as crystals of melting point 11° C.

Workup

  1. extractionextracted 3 times with ethyl acetate
  2. washwashed with water and sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customthe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-550cd8fd8733418b8b39f307fb939b52
Source dataset
uspto-grants-2004_01
Patent number
US06677324B1

Reaction notes

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