Acetic Acid → tert-Butyl 3-[4-cyclopropyl-5-[3-(2-ethylbutyl)cyclobutyl]isoxazol-3-yl]-5-hydroxyvalerate
Reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(O)(=O)C.[Si]([O:41][CH2:42][CH2:43][CH:44]([C:53]1[C:57]([CH:58]2[CH2:60][CH2:59]2)=[C:56]([CH:61]2[CH2:64][CH:63]([CH2:65][CH:66]([CH2:69][CH3:70])[CH2:67][CH3:68])[CH2:62]2)[O:55][N:54]=1)[CH2:45][C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>O1CCCC1>[CH:58]1([C:57]2[C:53]([CH:44]([CH2:43][CH2:42][OH:41])[CH2:45][C:46]([O:48][C:49]([CH3:51])([CH3:50])[CH3:52])=[O:47])=[N:54][O:55][C:56]=2[CH:61]2[CH2:62][CH:63]([CH2:65][CH:66]([CH2:69][CH3:70])[CH2:67][CH3:68])[CH2:64]2)[CH2:59][CH2:60]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To tetrabutylammonium fluoride (1 M in tetrahydrofuran) (6.26 mL) were added water (0.0725 mL), acetic acid (0.29 mL) and a solution of tert-butyl 5-(tert-butyldiphenylsilanyloxy)-3-{4-cyclopropyl-5-[3-(2-ethylbutyl)cyclobutyl]isoxazol-3-yl}valerate (2.76 g) in tetrahydrofuran (20 mL) at ice temperature. The mixture was stirred at RT overnight. The reaction mixture was concentrated in vacuo. The residue was purified by silica gel column chromatography (Eluent: ethyl acetate/hexane=1/6→1/4→1/2) to give the title compound (1.72 g).
Workup
- concentrationThe reaction mixture was concentrated in vacuo
- customThe residue was purified by silica gel column chromatography (Eluent: ethyl acetate/hexane=1/6→1/4→1/2)
Sources & evidence
- ORD record
- ord-e7d8715392f0478989f9c8cf5581c2b1
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08604069B2
Reaction notes
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