Hydrochloric Acid → HCID 22791147, compound

HRID 1658709Notes

Reaction equation

HRID 1658709 reaction equation
[C:1]([C@:3]1([OH:25])[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:19]([C@@H:20]([F:22])[CH2:21][C@:4]12[CH3:5])[C@:17]1([CH3:18])[C:12](=[CH:13][C:14](=[O:23])[CH2:15][CH2:16]1)[C@H:11]1O[C@@H:10]31)#[CH:2].[ClH:26]>C(O)(=O)C>[C:1]([C@:3]1([OH:25])[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:19]([C@@H:20]([F:22])[CH2:21][C@:4]12[CH3:5])[C@:17]1([CH3:18])[C:12](=[CH:13][C:14](=[O:23])[CH2:15][CH2:16]1)[C:11]([Cl:26])=[CH:10]3)#[CH:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22791150HCID 22791150, compound

Product 1

HCID 22791147HCID 22791147, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

460 mg. of 17α-ethinyl-6α,7α-epoxy-11β-fluoro-17β-hydroxy-4-androsten-3-one is introduced at room temperature into 25 ml. of glacial acetic acid saturated with gaseous hydrogen chloride. After 20 hours, the solution is poured into ice/water. The thus-precipitated product is vacuum-filtered and worked up as indicated in Example 17. After chromatography of the crude product on silica gel with acetone/hexane, 215 mg. of 17α-ethinyl-6-chloro-11β-fluoro-17β-hydroxy-4,6-androstadien-3-one is obtained as a foamy product. UV: ε282 = 20,600 (methanol).

Workup

  1. filtrationThe thus-precipitated product is vacuum-filtered

Sources & evidence

ORD record
ord-d6d3197f74b74b3794065c7670c734ef
Source dataset
uspto-grants-1976_06
Patent number
US03966713

Reaction notes

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