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

HRID 1837233Notes

Reaction equation

HRID 1837233 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].[F:30][C:31]([F:55])([C:51]([F:54])([F:53])[F:52])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]CC1C=C(C)C=CC=1S([O-])(=O)=O.[C:56](=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]([CH3:56])[CH2:28][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][C:31]([F:30])([F:55])[C:51]([F:52])([F:53])[F:54]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 1587066711beta-Fluoro-3-hydroxy-7alpha-[6-(methylamino)hexyl]oestra-1,3,5(10)-trien-17-oneHCID 234970369,9,10,10,10-Pentafluoro-decyltosylate

Product 1

HCID 1587066811beta-Fluoro-3-hydroxy-7alpha-{6-[methyl-(9,9,10,10,10-pentafluoro-decyl)-amino]-hexyl}-estra-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-(methyl-amino)-hexyl)-estra-1,3,5(10)-trien-17-one in 5 ml of dimethylformamide is stirred with 180 mg of 9,9,10,10,10-pentafluoro-decyltosylate for 2 hours 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. 121 mg of 11β-fluoro-3-hydroxy-7α-{6-[methyl-(9,9,10,10,10-pentafluoro-decyl)-amino]-hexyl}-estra-1,3,5(10)-trien-17-one is obtained as a foam, [α]D=+59° (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-fa13a09ed18d4078b193ee3ff4d6683a
Source dataset
uspto-grants-2004_08
Patent number
US06780855B2

Reaction notes

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