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

HRID 1912098ノート

反応式

HRID 1912098 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-e7d8715392f0478989f9c8cf5581c2b1
出典データセット
uspto-grants-2013_12
特許番号
US08604069B2

反応ノート

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