Hydrochloric Acid → HCID 23070781, compound
Reaction equation
Cl.[Si]([O:19][CH2:20][C:21]1[N:22]=[C:23]([N:34]2[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:36][CH2:35]2)[N:24]([CH2:30][C:31]#[C:32][CH3:33])[C:25]=1[C:26]([S:28][CH3:29])=N)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[O:47]1CCCC1>>[CH2:30]([N:24]1[C:25]([C:26]([S:28][CH3:29])=[O:47])=[C:21]([CH2:20][OH:19])[N:22]=[C:23]1[N:34]1[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:44])[CH3:45])=[O:41])[CH2:36][CH2:35]1)[C:31]#[C:32][CH3:33]Participants
Procedure
30 ml of 5N hydrochloric acid was added to a 100 ml tetrahydrofuran solution of 5.05 g of t-butyl 4-[4-(t-butyl diphenylsilanyloxymethyl)-1-(2-butynyl)-5-methylsulfanylcarbonimidoyl-1H-imidazol-2-yl]piperazine-1-carboxylate, and the mixture was stirred at room temperature for 22 hours. The solvent was concentrated under reduced pressure. The residue was dissolved in 100 ml of dichloromethane, and 2.05 g of di-t-butyl dicarbonate was added thereto. The solution was made alkaline with 5N sodium hydroxide, and stirred for 2 hours. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography. Thus, 2.24 g of the title compound was obtained from the fraction eluted with ethyl acetate-hexane (2:3).
Workup
- concentrationThe solvent was concentrated under reduced pressure
- dissolutionThe residue was dissolved in 100 ml of dichloromethane
- addition2.05 g of di-t-butyl dicarbonate was added
- stirringstirred for 2 hours
- dry with materialThe organic layer was dried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-9ce07846681740d7a30dfc4463b06282
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07772226B2
Reaction notes
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