Sodium Bicarbonate → 11beta-Fluoro-3-hydroxy-7alpha-{6-[methyl-(8,8,9,9,9-pentafluorononyl)-amino]hexyl}oestra-1,3,5(10)-trien-17-one

HRID 1838911Notes

Reaction equation

HRID 1838911 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]([OH:29])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][NH:27][CH3:28].S(C1C=CC(C)=CC=1)(OC[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][C:41]([F:47])([F:46])[C:42]([F:45])([F:44])[F:43])(=O)=O.[C:55](=O)([O-])O.[Na+]>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:16]2=[O:20])[C@H:12]2[C@H:3]1[C:4]1[CH:5]=[CH:6][C:7]([OH:29])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][N:27]([CH3:55])[CH2:28][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][C:41]([F:46])([F:47])[C:42]([F:43])([F:44])[F:45]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 15858643HCID 15858643, compoundHCID 1587066711beta-Fluoro-3-hydroxy-7alpha-[6-(methylamino)hexyl]oestra-1,3,5(10)-trien-17-one

Product 1

HCID 8658764311beta-Fluoro-3-hydroxy-7alpha-{6-[methyl-(8,8,9,9,9-pentafluorononyl)-amino]hexyl}oestra-1,3,5(10)-trien-17-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 381 mg of 11β-fluoro-3-hydroxy-7α-[6-(methylamino)hexyl]oestra-1,3,5(10)-trien-17-one in 5 ml of dimethylformamide is stirred at a bath temperature of 100° C. for 2 hours with 200 mg of 8,8,9,9,9-pentafluorononyl tosylate. It is then added to half-saturated sodium hydrogencarbonate solution, extracted three times with methylene chloride, dried over magnesium sulphate, concentrated in vacuo and chromatographed on silica gel using dichloromethane/methanol. 90 mg of 11β-fluoro-3-hydroxy-7α-{6-[methyl-(8,8,9,9,9-pentafluorononyl)-amino]hexyl}oestra-1,3,5(10)-trien-17-one are obtained as a foam.

Workup

  1. extractionextracted three times with methylene chloride
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated in vacuo
  4. customchromatographed on silica gel

Sources & evidence

ORD record
ord-60665477d3d1446ca6d2acd3b564e39d
Source dataset
uspto-grants-2004_01
Patent number
US06677324B1

Reaction notes

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