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Hydrochloric Acid → 2-{3-[1-(3,5-Diethoxy-4-fluoro-benzyl)-piperidin-4-ylcarbamoyl]-phenoxy}-2-methyl-propionic acid

HRID 502390
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HRID 502390 반응식
C([O:3][C:4](=[O:38])[C:5]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15](=[O:37])[NH:16][CH:17]2[CH2:22][CH2:21][N:20]([CH2:23][C:24]3[CH:29]=[C:28]([O:30][CH2:31][CH3:32])[C:27]([F:33])=[C:26]([O:34][CH2:35][CH3:36])[CH:25]=3)[CH2:19][CH2:18]2)[CH:10]=1)([CH3:7])[CH3:6])C.[Li+].[OH-].O.Cl>C1COCC1.CO>[CH2:31]([O:30][C:28]1[CH:29]=[C:24]([CH:25]=[C:26]([O:34][CH2:35][CH3:36])[C:27]=1[F:33])[CH2:23][N:20]1[CH2:19][CH2:18][CH:17]([NH:16][C:15]([C:11]2[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=2)[O:8][C:5]([CH3:6])([CH3:7])[C:4]([OH:38])=[O:3])=[O:37])[CH2:22][CH2:21]1)[CH3:32]
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참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 684554712-{3-[1-(3,5-Diethoxy-4-fluoro-benzyl)-piperidin-4-ylcarbamoyl]-phenoxy}-2-methyl-propionic acid ethyl ester

생성물 1

HCID 684590972-{3-[1-(3,5-Diethoxy-4-fluoro-benzyl)-piperidin-4-ylcarbamoyl]-phenoxy}-2-methyl-propionic acid수율 26.9%

시약·촉매·용매 1

HCID 21899815
MeOH tetrahydrofuran
용매

실험 절차

0.54 g (1.0 mmol) of 2-{3-[1-(3,5-diethoxy-4-fluoro-benzyl)-piperidin-4-ylcarbamoyl]-phenoxy}-2-methyl-propionic acid ethyl ester (example 50k) was reacted with 1.0 mL of LiOH/water (1.0 molar) in 15 mL of THF/MeOH (2:1) at 0° C. and subsequent temperature increase to rt. After 5 h, the reaction mixture was poured into crashed ice, the pH was adjusted to ˜7.0 with aq. HCl (1N) and the reaction mixture was extracted twice with MeCl2; the organic phases were washed with water, dried over MgSO4, filtered and evaporated i.V. The crude product was purified by chromatography (silicagel, eluent:gradient of MeCl2/MeOH) to yield 0.135 g of the title compound as colorless solid. MS: 503.1 (MH+).

후처리

  1. additionthe reaction mixture was poured
  2. extractionthe reaction mixture was extracted twice with MeCl2
  3. washthe organic phases were washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated i.V
  7. customThe crude product was purified by chromatography (silicagel, eluent:gradient of MeCl2/MeOH)

출처 및 근거

ORD 기록
ord-eca27cca77a246f891910ada7d26a9b7
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07772253B2

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