Acetic Acid → HCID 71127315, compound
Reaction equation
[Si]([O:18][CH2:19][CH2:20][CH:21]([C:30]1[N:31]=[N:32][N:33]([CH:38]2[CH2:41][CH:40]([CH2:42][CH:43]([CH3:45])[CH3:44])[CH2:39]2)[C:34]=1[CH:35]1[CH2:37][CH2:36]1)[CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=O)C>[Cl-].[Na+].O>[CH:35]1([C:34]2[N:33]([CH:38]3[CH2:39][CH:40]([CH2:42][CH:43]([CH3:45])[CH3:44])[CH2:41]3)[N:32]=[N:31][C:30]=2[CH:21]([CH2:20][CH2:19][OH:18])[CH2:22][C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])[CH2:36][CH2:37]1Participants
Procedure
tert-Butyl 5-(tert-butyldiphenylsilanyloxy)-3-[5-cyclopropyl-1-(3-isobutylcyclobutyl)-1H-[1,2,3]triazol-4-yl]valerate (233 mg) and tetrahydrofuran (3.0 mL) were mixed. To the mixture were added tetrabutylammonium fluoride (1 M in tetrahydrofuran) (0.444 mL) and 80 v/v % aqueous acetic acid (0.045 mL) at ice temperature. The mixture was stirred at RT overnight. After an addition of brine at ice temperature, the mixture was extracted with ethyl acetate. The organic layer was washed with brine, then dried over magnesium sulfate. The magnesium sulfate was filtered off and the filtrate was concentrated in vacuo. The resultant residue was purified by silica gel column chromatography (Eluent: ethyl acetate/hexane=1/2) to give the title compound (107 mg).
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried over magnesium sulfate
- filtrationThe magnesium sulfate was filtered off
- concentrationthe filtrate was concentrated in vacuo
- customThe resultant residue was purified by silica gel column chromatography (Eluent: ethyl acetate/hexane=1/2)
Sources & evidence
- ORD record
- ord-8904817a67244b9a9f278969b225d92f
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08604069B2
Reaction notes
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