Hydrochloric Acid → (17beta)-7-methyl-3-oxo-N-[2-(trifluoromethyl)phenyl]androst-4-ene-17-carboxamide

HRID 749054Notes

Reaction equation

HRID 749054 reaction equation
[CH3:1][CH:2]1[CH:19]=[C:18]2[C@:13]([CH3:21])([CH2:14][CH2:15][C:16](=[O:20])[CH2:17]2)[C@@H:12]2[C@@H:3]1[C@H:4]1[C@@:8]([CH2:10][CH2:11]2)([CH3:9])[C@@H:7]([C:22]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]([F:34])([F:33])[F:32])=[O:23])[CH2:6][CH2:5]1.Cl>O1CCOCC1>[CH3:1][CH:2]1[CH2:19][C:18]2[C@:13]([CH3:21])([CH2:14][CH2:15][C:16](=[O:20])[CH:17]=2)[C@@H:12]2[C@@H:3]1[C@H:4]1[C@@:8]([CH2:10][CH2:11]2)([CH3:9])[C@@H:7]([C:22]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]([F:32])([F:33])[F:34])=[O:23])[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69266012(17beta)-7-methyl-3-oxo-N-[2-(trifluoromethyl)phenyl]androst-5-ene-17-carboxamide

Product 1

HCID 68973006(17beta)-7-methyl-3-oxo-N-[2-(trifluoromethyl)phenyl]androst-4-ene-17-carboxamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of the compound from Step B (5-3) (0.057 g, 0.12 mmol), dioxane (0.5 mL) and 1.0 N HCl solution (0.5 mL) was heated to 50° C. for 2 hr. The reaction was then concentrated to yield the desired product as an 8:1 mixture of epimers at C-7.

Workup

  1. concentrationThe reaction was then concentrated

Sources & evidence

ORD record
ord-8d3abedac6364aa389fc4ede506398eb
Source dataset
uspto-grants-2008_07
Patent number
US07402577B2

Reaction notes

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