Hydrochloric Acid → HCID 68146606, compound

HRID 1658711Notes

Reaction equation

HRID 1658711 reaction equation
C(O[C@H]1CC[C@H]2[C@H]3[C@H]([C@@H](F)C[C@]12C)[C@]1(C)C(=CC(=O)CC1)CC3)(=O)C.ClN1C(=O)CCC1=O.[C:34]([O:37][C@H:38]1[CH2:43][CH2:42][C@H:41]2[C@H:44]3[C@H:54]([C@@H:55]([F:57])[CH2:56][C@:39]12[CH3:40])[C@:52]1([CH3:53])[C:47](=[CH:48][C:49](=[O:58])[CH2:50][CH2:51]1)[C@H:46]([Cl:59])[CH2:45]3)(=[O:36])[CH3:35].Cl>C(Cl)Cl.C(O)(=O)C.C(Cl)(Cl)Cl.O.CC(C)=O>[C:34]([O:37][C@H:38]1[CH2:43][CH2:42][C@H:41]2[C@H:44]3[C@H:54]([C@@H:55]([F:57])[CH2:56][C@:39]12[CH3:40])[C@:52]1([CH3:53])[C:47](=[CH:48][C:49](=[O:58])[CH2:50][CH2:51]1)[C@@H:46]([Cl:59])[CH2:45]3)(=[O:36])[CH3:35]

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 31398ChlorosuccinimideHCID 68146532HCID 68146532, compoundHCID 68147202HCID 68147202, compound

Product 1

HCID 68146606HCID 68146606, compound

Reagents, catalysts & solvents 5

HCID 176Acetic AcidSolventHCID 180AcetoneSolventHCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.8 g. of 17β-acetoxy-11β-fluoro-4-androsten-3-one in 60 ml. of acetone and 12 ml. of water is combined with 2.6 g. of N-chlorosuccinimide; the reaction mixture is allowed to stand for 1 day at room temperature. Then, the solution is diluted with methylene chloride, washed successively with sodium thiosulfate solution and water, and dried over sodium sulfate. Chromatography of the crude product on silica gel with acetone/hexane yields 1.1 g. of 17β-acetoxy-6β-chloro-11β-fluoro-4-androsten-3-one. This product is dissolved in 100 ml. of chloroform and combined with 6 ml. of glacial acetic acid saturated with gaseous hydrogen chloride. The solution is allowed to stand at 0° for 2 hours and then introduced into ice/water. The precipitate is vacuum-filtered, washed with water, and dried. After purification by means of preparative layer chromatography (hexane/ethyl acetate 7 : 3), 530 mg. of 17β-acetoxy-6α-chloro-11β-fluoro-4-androsten-3-one is isolated as an oil. UV: ε236 = 15,400 (methanol).

Workup

  1. washwashed successively with sodium thiosulfate solution and water
  2. dry with materialdried over sodium sulfate
  3. customChromatography of the crude product on silica gel with acetone/hexane yields 1.1 g
  4. dissolutionThis product is dissolved in 100 ml
  5. waitto stand at 0° for 2 hours
  6. filtrationThe precipitate is vacuum-filtered
  7. washwashed with water
  8. customdried
  9. customAfter purification by means of preparative layer chromatography (hexane/ethyl acetate 7 : 3), 530 mg

Sources & evidence

ORD record
ord-60b36fbf8c79411cbb2a21d4de755505
Source dataset
uspto-grants-1976_06
Patent number
US03966713

Reaction notes

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