Perchloric Acid → 17alpha-Hydroxy-3-oxo-4-androstene-17-carboxylic acid amide
Reaction equation
[OH:1][C@:2]1([C:22]#[N:23])[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C:11](=[CH:12][C:13](=[O:21])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3.Cl(O)(=O)(=O)=[O:25]>C(O)(=O)C.C(OC(=O)C)(=O)C>[OH:1][C@:2]1([C:22]([NH2:23])=[O:25])[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C:11](=[CH:12][C:13](=[O:21])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3Participants
5
Conditions
- Temperature
- 20 °C
Procedure
A solution of 6.26 g of 17α-hydroxy-17-cyano-4-androsten-3-one in 50 ml of glacial acetic acid and 50 ml of acetic anhydride is combined with 0.5 ml of 70% perchloric acid, and the mixture is allowed to stand for 1 hour at 20° C. The product is precipitated into ice water, filtered off, and then dissolved in 570 ml of methanol. This solution is combined with 61 ml of a 1 N potassium hydroxide solution, and the mixture is stirred overnight at 20° C. The methanolic solution is diluted with 500 g of ice water, the precipitated product is vacuum-filtered and dried. Repeated crystallization from ethyl acetate--methylene chloride yields 5.62 g of 17α-hydroxy-3-oxo-4-androstene-17-carboxylic acid amide, mp 271°-273.5° C.
Workup
- customThe product is precipitated into ice water
- filtrationfiltered off
- dissolutiondissolved in 570 ml of methanol
- additionThe methanolic solution is diluted with 500 g of ice water
- filtrationthe precipitated product is vacuum-filtered
- customdried
- customcrystallization from ethyl acetate
Sources & evidence
- ORD record
- ord-4c3c238c0d5a4fe38a8145f9cba8965f
- Source dataset
- uspto-grants-1982_09
- Patent number
- US04348327
Reaction notes
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