Potassium Hydroxide → HCID 260703, compound
Reaction equation
C([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C:14]2=[N:24][OH:25])[CH2:6]1)(=O)C.[OH-].[K+]>>[N:24](=[C:14]1[CH2:13][CH2:12][C@H:11]2[C@H:10]3[C@H:19]([CH2:18][CH2:17][C@:15]12[CH3:16])[C@:20]1([CH3:23])[C:7]([CH2:6][C@@H:5]([OH:4])[CH2:22][CH2:21]1)=[CH:8][CH2:9]3)[OH:25]Participants
Procedure
17-Oximino-5-androsten-3β-yl acetate (8) was hydrolyzed with methanolic potassium hydroxide to get 17-oximino-5-androsten-3β-ol (9). In 1H-NMR spectrum signals for 3α and 6-vinylic protons appeared at δ 4.54 and δ 5.22, respectively. IR spectrum showed disappearance of the stretching due to acetate carbonyl at 1740 cm−1. 17-Oximino-5-androsten-3β-ol (9) was reacted with respective acid and dicyclohexylcarbodiimide (DCC) in anhydrous dichloromethane. The reaction mixture was stirred for 48 hr at room temperature and completion of the reaction was monitored by TLC. The precipitated dicyclohexylurea (DCU) was filtered, solvent removed under vacuum and the residue was crystallized from ethyl acetate:petroleum ether (60:80) to obtain the desired product.
Sources & evidence
- ORD record
- ord-c97d93d5fde64a20a70d7ce903879bad
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08435975B2
Reaction notes
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