Hydrochloric Acid → HCID 68949346, compound

HRID 650375Notes

Reaction equation

[Br-].[Li+].[Cl:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C@@H:9]1[CH2:26][C:25]2[C@H:20]([CH2:21][CH2:22][C:23](=[O:27])[CH:24]=2)[C@@H:19]2[C@@H:10]1[C@H:11]1[C@@:15]([CH2:17][C@@H:18]2[F:28])([CH3:16])[C:14](=[O:29])[CH2:13][CH2:12]1.C(=O)(O)[O-].[Na+].Cl>C(#N)C.[Cu](Br)Br.O>[Cl:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C@@H:9]1[CH2:26][C:25]2[CH:24]=[C:23]([OH:27])[CH:22]=[CH:21][C:20]=2[C@@H:19]2[C@@H:10]1[C@H:11]1[C@@:15]([CH2:17][C@@H:18]2[F:28])([CH3:16])[C:14](=[O:29])[CH2:13][CH2:12]1

Participants

Conditions

Temperature: 0 °C

Procedure

25.4 g of copper(II) bromide and 4.9 g of lithium bromide in 95 ml of anhydrous acetonitrile are added to 22.1 g of 7α-(5-chloropentyl)-11β-fluoro-estr-4-ene-3,17-dione in 160 ml of anhydrous acetonitrile at 80° C. After 20 minutes, the reaction mixture is cooled to 0° C., and 200 ml of saturated sodium bicarbonate solution is added in drops. Then, the solution is stirred into 750 ml of water, brought to pH=6 with 2N hydrochloric acid, extracted 3 times with ethyl acetate, washed with common salt solution, dried on magnesium sulfate and concentrated by evaporation in a vacuum. Chromatography of the crude product on silica gel with a hexane-ethyl acetate gradient yields 14.7 g of 7α-(5-chloropentyl)-11β-fluoro-3-hydroxy-estra-1,3,5(10)-trien-17-one.

Workup

extractionextracted 3 times with ethyl acetate
washwashed with common salt solution
customdried on magnesium sulfate
concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record: ord-89b78e3294b347b7af40b48651e5f37a
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06271403B1

Reaction notes

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