Sodium Chloride → 11beta-Fluor-7alpha-{5-[methyl-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-nonyl)-amino]-pentyl}-estra-1,3,5(10)-triene-3,17beta-diol

HRID 1837239Notes

Reaction equation

HRID 1837239 reaction equation
BrC[CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:24][C:23]2[CH:22]=[C:21]([OH:25])[CH:20]=[CH:19][C:18]=2[C@@H:17]2[C@@H:8]1[C@H:9]1[C@@:13]([CH2:15][C@@H:16]2[F:26])([CH3:14])[CH:12]([OH:27])[CH2:11][CH2:10]1.[CH3:28][NH:29][CH2:30][CH2:31][CH2:32][C:33]([F:51])([F:50])[C:34]([F:49])([F:48])[C:35]([F:47])([F:46])[C:36]([F:45])([F:44])[C:37]([F:43])([F:42])[C:38]([F:41])([F:40])[F:39].[Cl-].[Na+].[CH3:54]N1CCCC1=O>>[F:26][C@H:16]1[CH2:15][C@@:13]2([CH3:14])[C@@H:9]([CH2:10][CH2:11][C@@H:12]2[OH:27])[C@H:8]2[C@H:17]1[C:18]1[CH:19]=[CH:20][C:21]([OH:25])=[CH:22][C:23]=1[CH2:24][C@H:7]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:28][N:29]([CH3:54])[CH2:30][CH2:31][CH2:32][C:33]([F:50])([F:51])[C:34]([F:49])([F:48])[C:35]([F:46])([F:47])[C:36]([F:44])([F:45])[C:37]([F:42])([F:43])[C:38]([F:40])([F:39])[F:41]

Participants

5

Reactant 4

HCID 5234Sodium ChlorideHCID 13387N-methyl-2-pyrrolidoneHCID 234971254,4,5,5,6,6,7,7,8,8,9,9,9-Tridecafluoro-N-methylnonan-1-amineHCID 699180487alpha-(5-Bromopentyl)-11beta-fluor-estra-1,3,5(10)-triene-3,17-diol

Product 1

HCID 1585865011beta-Fluor-7alpha-{5-[methyl-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-nonyl)-amino]-pentyl}-estra-1,3,5(10)-triene-3,17beta-diol

Procedure

A solution of 466 mg of 7α-(5-bromopentyl)-11β-fluor-estra-1,3,5(10)-triene-3,17-diol in 10 ml of 1-methyl-2-pyrrolidinone is stirred with 1.17 g of methyl-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononyl)-amine for 3 hours at a bath temperature of 80° C. For working-up, the batch is added to saturated sodium chloride solution, extracted with ethyl acetate, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with dichloromethane/methanol. 625 mg of 11β-fluor-7α-{5-[methyl-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-nonyl)-amino]-pentyl}-estra-1,3,5(10)-triene-3,17β-diol is obtained as a foam, [α]D=+35° (c=0.5 in CHCl3).

Workup

  1. extractionextracted with ethyl acetate
  2. customdried on sodium sulfate
  3. concentrationconcentrated by evaporation in a vacuum
  4. customchromatographed on silica gel with dichloromethane/methanol

Sources & evidence

ORD record
ord-a8e3b8a78e384225bfdf19568307ccc5
Source dataset
uspto-grants-2004_08
Patent number
US06780855B2

Reaction notes

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