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Lithium hydroxide, monohydrate → 4-isopropyl-2-(N-tert-butoxycarbonylpiperidin-3-yl)methoxybenzoic acid

HRID 1787900
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인쇄 미리보기

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HRID 1787900 반응식
[CH:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10]C)=[O:9])=[C:6]([O:14][CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]2)[CH:5]=1)([CH3:3])[CH3:2].O[Li].O>C1COCC1.O>[C:25]([O:24][C:22]([N:18]1[CH2:19][CH2:20][CH2:21][CH:16]([CH2:15][O:14][C:6]2[CH:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:13]=[CH:12][C:7]=2[C:8]([OH:10])=[O:9])[CH2:17]1)=[O:23])([CH3:28])([CH3:27])[CH3:26]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 68573359Methyl 2-(1-tert-Butoxycarbonylpiperidin-3-ylmethoxy)-4-isopropylbenzoate

생성물 1

HCID 685322644-isopropyl-2-(N-tert-butoxycarbonylpiperidin-3-yl)methoxybenzoic acid수율 83.6%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
65 °C

실험 절차

The methyl 4-isopropyl-2-(1-tert-butoxycarbonyl-piperidin-3-ylmethoxy)benzoate (1.53 g, 3.90 mmol) was dissolved in THF (15 mL). Then LiOH.H2O (0.36 g, 8.58 mmol) in water (5 mL) was added. The mixture was heated at 65° C. for 24 h. The reaction mixture was concentrated in vacuo and then redissolved in a mixture of EtOAc (100 mL) and cold dilute HCl. The mixture was shaken in a separatory funnel. The layers were separated and the organic layer was washed with cold water (100 mL), dried (MgSO4), and concentrated to give 1.23 g of the title compound as an oil.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionredissolved in a mixture of EtOAc (100 mL) and cold dilute HCl
  3. customThe layers were separated
  4. washthe organic layer was washed with cold water (100 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-64265ceffcb246c196f3dc6e771ef307
출처 데이터셋
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07511066B2

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