Hydrochloric Acid → HCID 68146617, compound

HRID 1658706Notes

Reaction equation

HRID 1658706 reaction equation
[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([C@@H:22]([F:24])[CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C:14](=[CH:15][C:16](=[O:25])[CH2:17][CH2:18]1)[C@H:13]1O[C@@H:12]31)(=[O:3])[CH3:2].[ClH:27]>C(O)(=O)C>[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([C@@H:22]([F:24])[CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C:14](=[CH:15][C:16](=[O:25])[CH2:17][CH2:18]1)[C:13]([Cl:27])=[CH:12]3)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86733596HCID 86733596, compound

Product 1

HCID 68146617HCID 68146617, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

500 mg. of 17β-acetoxy-6α,7α-epoxy-11β-fluoro-4-androsten-3-one is introduced at room temperature into 25 ml. of glacial acetic acid saturated with gaseous hydrogen chloride. After 24 hours, the solution is poured into ice/water. The thus-precipitated product is vacuum-filtered, taken up in methylene chloride, washed with water, and dried. After recrystallization of the crude product from acetone/hexane, 210 mg. of 17β-acetoxy-6-chloro-11β-fluoro-4,6-androstadien-3-one is obtained. UV: ε283 = 20,300.

Workup

  1. filtrationThe thus-precipitated product is vacuum-filtered
  2. washwashed with water
  3. customdried
  4. customAfter recrystallization of the crude product from acetone/hexane, 210 mg

Sources & evidence

ORD record
ord-effb44c1ad2d4164a07712981b798120
Source dataset
uspto-grants-1976_06
Patent number
US03966713

Reaction notes

Loading…