Acetic Acid → tert-Butyl 3-[4-cyclopropyl-5-[3-(2-ethylbutyl)cyclobutyl]isoxazol-3-yl]-5-hydroxyvalerate

HRID 1912098노트

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HRID 1912098 반응식
[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]1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 71114789tert-Butyl 5-(tert-butyldiphenylsilanyloxy)-3-{4-cyclopropyl-5-[3-(2-ethylbutyl)cyclobutyl]isoxazol-3-yl}valerate

생성물 1

HCID 71127337tert-Butyl 3-[4-cyclopropyl-5-[3-(2-ethylbutyl)cyclobutyl]isoxazol-3-yl]-5-hydroxyvalerate수율 97.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was purified by silica gel column chromatography (Eluent: ethyl acetate/hexane=1/6→1/4→1/2)

출처 및 근거

ORD 기록
ord-e7d8715392f0478989f9c8cf5581c2b1
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604069B2

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