Sodium Bicarbonate → 11beta-Fluoro-3-hydroxy-7alpha-{5-[methyl-(9,9,10,10,10-pentafluoro-decyl)-amino]-pentyl}-estra-1,3,5(10)-trien-17-one

HRID 1837226Notes

Reaction equation

HRID 1837226 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:28])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][CH3:27].[F:29][C:30]([F:54])([C:50]([F:53])([F:52])[F:51])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]COS(C1C=CC(C)=CC=1)(=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:28])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([CH3:55])[CH2:27][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][C:30]([F:29])([F:54])[C:50]([F:51])([F:52])[F:53]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 1587066511beta-Fluoro-3-hydroxy-7alpha-[5-(methylamino)-pentyl]-estra-1,3,5(10)-trien-17-oneHCID 572649069,9,10,10,10-Pentafluorodecyltosylate

Product 1

HCID 1587066611beta-Fluoro-3-hydroxy-7alpha-{5-[methyl-(9,9,10,10,10-pentafluoro-decyl)-amino]-pentyl}-estra-1,3,5(10)-trien-17-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 260 mg of 11β-fluoro-3-hydroxy-7α-[5-(methyl-amino)-pentyl]-estra-1,3,5(10)-trien-17-one in 3 ml of dimethylformamide is stirred with 180 mg of 9,9,10,10,10-pentafluorodecyltosylate for 1 hour at a bath temperature of 100° C. Then, it is added to semi-saturated sodium bicarbonate solution, extracted three times with methylene chloride, dried on magnesium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with dichloromethane/methanol/triethylamine. 92 mg of 11β-fluoro-3-hydroxy-7α-{5-[methyl-(9,9,10,10,10-pentafluoro-decyl)-amino]-pentyl}-estra-1,3,5(10)-trien-17-one is obtained as a foam, [α]D=+48° (c=1.0 in chloroform).

Workup

  1. extractionextracted three times with methylene chloride
  2. customdried on magnesium sulfate
  3. concentrationconcentrated by evaporation in a vacuum
  4. customchromatographed on silica gel with dichloromethane/methanol/triethylamine

Sources & evidence

ORD record
ord-3db66fd61c96487b967f4803a8ce3683
Source dataset
uspto-grants-2004_08
Patent number
US06780855B2

Reaction notes

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