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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
ノート
印刷プレビュー

反応式

HRID 502390 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21899815
MeOH tetrahydrofuran
溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-eca27cca77a246f891910ada7d26a9b7
出典データセット
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07772253B2

反応ノート

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