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Lithium Hydroxide → (+/-)-3-(4-Ethylpyridin-2-yl)-4-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)butanoic Acid

HRID 2099755
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HRID 2099755 반응식
[CH2:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH:9]([CH2:16][C:17]2[CH:25]=[C:24]([CH3:26])[C:23]3[C:19](=[CH:20][N:21]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[N:22]=3)[CH:18]=2)[CH2:10][C:11]([O:13]CC)=[O:12])[CH:4]=1)[CH3:2].[OH-].[Li+]>O1CCCC1>[CH2:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH:9]([CH2:16][C:17]2[CH:25]=[C:24]([CH3:26])[C:23]3[C:19](=[CH:20][N:21]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:32])([CH3:34])[CH3:33])[N:22]=3)[CH:18]=2)[CH2:10][C:11]([OH:13])=[O:12])[CH:4]=1)[CH3:2]
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HCID 3939Lithium HydroxideHCID 57794570(+/-)-Ethyl 3-(4-ethylpyridin-2-yl)-4-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)butanoate

생성물 1

HCID 57794674(+/-)-3-(4-Ethylpyridin-2-yl)-4-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)butanoic Acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

To a flask containing (±)-ethyl 3-(4-ethylpyridin-2-yl)-4-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)butanoate (80 mg, 0.166 mmol, 1.0 equiv) in tetrahydrofuran (4 mL) was added lithium hydroxide (2.0 M, 0.34 mL, 4.0 equiv). The suspension was heated at 60° C. under nitrogen overnight. The reaction mixture was concentrated in vacuo. Hydrochloric acid (1 N, 0.6 mL) was added and the solution was extracted with ethyl acetate. The aqueous solution was adjusted to pH 7 with sodium hydroxide (1 N) and re-extracted with ethyl acetate. The combined ethyl acetate layers were washed with brine, dried over sodium sulfate and concentrated in vacuo to give a light yellow oil. MS (ESI) 454 (MH)+.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionHydrochloric acid (1 N, 0.6 mL) was added
  3. extractionthe solution was extracted with ethyl acetate
  4. extractionre-extracted with ethyl acetate
  5. washThe combined ethyl acetate layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto give a light yellow oil

출처 및 근거

ORD 기록
ord-744c724ff79648e6b2ec58ce1045cd6a
출처 데이터셋
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07569578B2

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