Water → HCID 15858644, compound

HRID 1837212Notes

Reaction equation

HRID 1837212 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][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][CH3:27].[F:29][C:30]([F:53])([C:49]([F:52])([F:51])[F:50])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]C1C=C(C)C=CC=1S([O-])(=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])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][C:30]([F:29])([F:53])[C:49]([F:50])([F:51])[F:52]

Participants

5

Reactant 3

HCID 962WaterHCID 15858642HCID 15858642, compoundHCID 234971528,8,9,9,9-Pentafluoro-nonyltosylate

Product 1

HCID 15858644HCID 15858644, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.77 g of 11β-fluoro-7α-[5-(methyl-amino)-pentyl]-estra-1,3,5(10)-triene-3,17β-diol in 18 ml of dimethylformamide is stirred with 1.4 g of 8,8,9,9,9-pentafluoro-nonyltosylate for 1 hour at a bath temperature of 80° C. Then, it is added to water, extracted three times with ethyl acetate, washed with water and common salt solution, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with dichloromethane/methanol. 11β-Fluoro-7α-{5-[methyl-(8,8,9,9,9-pentafluoro-nonyl)-amino]-pentyl}-estra-1,3,5(10)-triene-3,17β-diol is obtained as crystals with a melting point of 110° C.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washwashed with water and common salt solution
  3. customdried on sodium sulfate
  4. concentrationconcentrated by evaporation in a vacuum
  5. customchromatographed on silica gel with dichloromethane/methanol

Sources & evidence

ORD record
ord-32e66745a8314835a06ef076e64e5c39
Source dataset
uspto-grants-2004_08
Patent number
US06780855B2

Reaction notes

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