Tetrahydrofuran → tert-Butyl 3-[4-cyclopropyl-5-(3-isobutylcyclobutyl)isoxazol-3-yl]-5-hydroxyvalerate

HRID 1912055Notes

Reaction equation

HRID 1912055 reaction equation
[Si]([O:18][CH2:19][CH2:20][CH:21]([C:30]1[C:34]([CH:35]2[CH2:37][CH2:36]2)=[C:33]([CH:38]2[CH2:41][CH:40]([CH2:42][CH:43]([CH3:45])[CH3:44])[CH2:39]2)[O:32][N:31]=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.O>[CH:35]1([C:34]2[C:30]([CH:21]([CH2:20][CH2:19][OH:18])[CH2:22][C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])=[N:31][O:32][C:33]=2[CH:38]2[CH2:39][CH:40]([CH2:42][CH:43]([CH3:45])[CH3:44])[CH2:41]2)[CH2:36][CH2:37]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 71127323tert-Butyl 5-(tert-butyldiphenylsilanyloxy)-3-[4-cyclopropyl-5-(3-isobutylcyclobutyl)isoxazol-3-yl]valerate

Product 1

HCID 71127324tert-Butyl 3-[4-cyclopropyl-5-(3-isobutylcyclobutyl)isoxazol-3-yl]-5-hydroxyvalerateYield 107.9%

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Procedure

tert-Butyl 5-(tert-butyldiphenylsilanyloxy)-3-[4-cyclopropyl-5-(3-isobutylcyclobutyl)isoxazol-3-yl]valerate (17.62 g) and tetrahydrofuran (106 mL) were mixed. After an addition of acetic acid/water=4/1 (2.45 mL) and tetrabutylammonium fluoride (1 M in tetrahydrofuran) (39.2 mL) to the solution at ice temperature, the mixture was stirred at RT overnight. The reaction mixture was concentrated in vacuo and purified by silica gel column chromatography (Eluent: ethyl acetate/hexane=1/6→1/2) to give the title compound (11.82 g).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by silica gel column chromatography (Eluent: ethyl acetate/hexane=1/6→1/2)

Sources & evidence

ORD record
ord-8fcf07a46a0a48598e39a50cb28a20af
Source dataset
uspto-grants-2013_12
Patent number
US08604069B2

Reaction notes

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