Ethyl Acetate → 6alpha-Fluoro-9alpha-bromo-11beta-hydroxy-16beta-methyl-17alpha,21-diacetoxypregna-1,4-diene-3,20-dione

HRID 1680474Notes

Reaction equation

HRID 1680474 reaction equation
[F:1][C@@H:2]1[C:25]2[C@:20](C)([CH:21]=[CH:22][C:23](=[O:26])[CH:24]=2)[C:19]2[C@H:4]([C@H:5]3[C@:16]([CH3:28])([CH2:17]C=2)[C@@:8]([O:29][C:30](=[O:32])[CH3:31])([C:9](=[O:15])[CH2:10][O:11][C:12](=[O:14])[CH3:13])[C@@H:7]([CH3:33])[CH2:6]3)[CH2:3]1.Br[C:35]1([Br:42])NC(=O)N[C:36]1=[O:41].C(OCC)(=O)C>O1CCOCC1.O>[F:1][C@@H:2]1[C:25]2[C@:20]([CH3:19])([CH:21]=[CH:22][C:23](=[O:26])[CH:24]=2)[C@:35]2([Br:42])[C@H:4]([C@H:5]3[C@:16]([CH3:17])([CH2:28][C@@H:36]2[OH:41])[C@@:8]([O:29][C:30](=[O:32])[CH3:31])([C:9](=[O:15])[CH2:10][O:11][C:12](=[O:14])[CH3:13])[C@@H:7]([CH3:33])[CH2:6]3)[CH2:3]1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 54068228DibromohydantoinHCID 703696486alpha-Fluoro-16beta-methyl-17alpha,21-diacetoxypregna-1,4,9(11)-triene-3,20-dione

Product 1

HCID 228154806alpha-Fluoro-9alpha-bromo-11beta-hydroxy-16beta-methyl-17alpha,21-diacetoxypregna-1,4-diene-3,20-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Ten (10) g of 6α-fluoro-16β-methyl-17α,21-diacetoxypregna-1,4,9(11)-triene-3,20-dione in 110 ml of dioxane (A.R.) plus 2.2 mls of a solution of 4.4 ml 70% HClO4 in 200 mls of water, is treated with 4 g of dibromohydantoin in the dark at R.T. for a period of one hour or when TLC using 50% ethyl acetate/50% hexane shows the reaction to be complete. The reaction mixture is precipitated in 2 of water, stirred for 10 minutes and the crystalline precipitate collected by filtration, washed with water, and air dried to give 11.4 g of 6α-fluoro-9α-bromo-11β-hydroxy-16β-methyl-17α,21-diacetoxypregna-1,4-diene-3,20-dione.

Workup

  1. customthe reaction
  2. customThe reaction mixture is precipitated in 2 of water
  3. filtrationthe crystalline precipitate collected by filtration
  4. washwashed with water, and air
  5. customdried

Sources & evidence

ORD record
ord-afb2bcf43bf04714a61d1adc42b07598
Source dataset
uspto-grants-1981_06
Patent number
US04273770

Reaction notes

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