Ammonia → HCID 70627028, compound

HRID 616348Notes

Reaction equation

HRID 616348 reaction equation
[C:1]([O:4][C@:5]1([C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C:22](=[CH:23][CH2:24]2)[C@:20]2([CH3:21])[C:15](=[CH:16][C:17](=[O:28])[C@@H:18]4[CH2:27][C@@H:19]42)[C:14]([Cl:29])=[CH:13]3)[CH2:10][CH2:9]1)[C:6](=[O:8])[CH3:7])(=[O:3])[CH3:2].[Br:30]N1C(=O)CCC1=O.[FH:38].N>N1C=CC=CC=1>[C:1]([O:4][C@:5]1([C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@:22]([Br:30])([C@@H:23]([F:38])[CH2:24]2)[C@:20]2([CH3:21])[C:15](=[CH:16][C:17](=[O:28])[C@@H:18]4[CH2:27][C@@H:19]42)[C:14]([Cl:29])=[CH:13]3)[CH2:10][CH2:9]1)[C:6](=[O:8])[CH3:7])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 14917Hydrofluoric AcidHCID 67184N-bromobutanimideHCID 70626483HCID 70626483, compound

Product 1

HCID 70627028HCID 70627028, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

At -30° C., 1.5 g. of 17-acetoxy-6-chloro-1α,2α -methylene-4,6,9(11)-pregnatriene-3,20 -dione and 1.5 g. of N-bromosuccinimide are added in succession to 7.5 ml. of a 70% solution of hydrogen fluoride in pyridine. After 1.5 hours, the solution is introduced into a mixture of ice water and 25% ammonia solution. The thus-precipitated product is vacuum-filtered, washed with water, dissolved in ethyl acetate, and dried over sodium sulfate. The crude product is recrystallized from acetone/hexane. Yield: 836 mg. of 17-acetoxy-9-bromo-6-chloro-11β-fluoro-1α,2α -methylene-4,6-pregnadiene-3,20 -dione; m.p. 189°-191° C. (under decomposition). UV: ε283 = 13,400.

Workup

  1. customAt -30° C.
  2. filtrationThe thus-precipitated product is vacuum-filtered
  3. washwashed with water
  4. dissolutiondissolved in ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. customThe crude product is recrystallized from acetone/hexane

Sources & evidence

ORD record
ord-4d198ad3e9c44a2ab561ab78ef55cb2f
Source dataset
uspto-grants-1978_02
Patent number
US04073900

Reaction notes

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