Hydrochloric Acid → HCID 86743651, compound
Reaction equation
[CH:1]1(NC(C)C)CCCCC1.C([Li])CCC.[CH2:16]([O:18][C:19]([C@@H:21]1[CH2:45][CH2:44][C@@:43]2([CH3:46])[C@H:23]([CH2:24][C@H:25]([C:49]([O:51][CH2:52][CH3:53])=[O:50])[C@@H:26]3[C@@H:42]2[CH2:41][C@H:40]([OH:47])[C@@:39]2([CH3:48])[C@H:27]3[CH2:28][CH2:29][C@@H:30]2[C@H:31]([CH3:38])[CH2:32][CH2:33][C:34]([O:36][CH3:37])=[O:35])[CH2:22]1)=[O:20])[CH3:17].CI.Cl>C1COCC1>[CH2:16]([O:18][C:19]([C@@H:21]1[CH2:45][CH2:44][C@@:43]2([CH3:46])[C@H:23]([CH2:24][C@H:25]([C:49]([O:51][CH2:52][CH3:53])=[O:50])[C@@H:26]3[C@@H:42]2[CH2:41][C@H:40]([OH:47])[C@@:39]2([CH3:48])[C@H:27]3[CH2:28][CH2:29][C@@H:30]2[C@H:31]([CH3:38])[CH2:32][CH:33]([CH3:1])[C:34]([O:36][CH3:37])=[O:35])[CH2:22]1)=[O:20])[CH3:17]Participants
Conditions
- Temperature
- -78 °C
Procedure
To a solution of N-cyclohexyl-isopropyl-amine (2.8 ml: 0.017 mol) in anhydrous THF (120 ml), 11.4 ml (0.016 mol) of a butyllithium solution were added in 30'; the stirred mixture was then cooled (under nitrogen) to -78° C., and 3α,7β-diethoxycarbonyl-12α-hydroxy-5β-cholan-24-oic acid, methyl ester (2.5 g; 0.0045 mol), dissolved in 22 ml of anhydrous THF was added very slowly (45'). Fifteen minutes after the addition, CH3I (10.2 g; 0.072 mol) was added, and the mixture was brought to room temperature. After 5 hours the reaction was complete; the solution was acidified with a 10% aqueous solution of HCl and extracted with CHCl3 (3×80 ml). The chloroform solution was washed with water, dried on Na2SO4, and evaporated to dryness. The yield is almost quantitative.
Workup
- additionwas added very slowly (45')
- additionwas added
- customwas brought to room temperature
- extractionextracted with CHCl3 (3×80 ml)
- washThe chloroform solution was washed with water
- customdried on Na2SO4
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-1608e0db2a0f48d5b501b69f132bf725
- Source dataset
- uspto-grants-1991_01
- Patent number
- US04981983
Reaction notes
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