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Hydrochloric Acid → 3-[4-({[4'-(2-Ethoxyethoxy)-2',3',5',6'-tetramethylbiphenyl-3-yl]methyl}amino)-2-fluorophenyl]propanoic acid hydrochloride

HRID 508086
ノート
印刷プレビュー

反応式

HRID 508086 の反応式
[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[C:12]([CH3:13])=[C:11]([CH3:14])[C:10]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][NH:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31]([O:33]CC)=[O:32])=[C:25]([F:36])[CH:24]=3)[CH:16]=2)=[C:9]([CH3:37])[C:8]=1[CH3:38])[CH3:2].[OH-].[Na+].[ClH:41].Cl.C(OCC)(=O)C>CO.O1CCCC1.C(OCC)(=O)C>[ClH:41].[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[C:8]([CH3:38])=[C:9]([CH3:37])[C:10]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][NH:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[C:25]([F:36])[CH:24]=3)[CH:16]=2)=[C:11]([CH3:14])[C:12]=1[CH3:13])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21866389Hydrogen chloride-ethyl acetateHCID 23157425Ethyl 3-[4-({[4'-(2-ethoxyethoxy)-2',3',5',6'-tetramethylbiphenyl-3-yl]methyl}amino)-2-fluorophenyl]propanoate

生成物 1

HCID 866243843-[4-({[4'-(2-Ethoxyethoxy)-2',3',5',6'-tetramethylbiphenyl-3-yl]methyl}amino)-2-fluorophenyl]propanoic acid hydrochloride
収率 70%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
50 °C

実験手順

To a solution of ethyl 3-[4-({[4′-(2-ethoxyethoxy)-2′,3′,5′,6′-tetramethylbiphenyl-3-yl]methyl}amino)-2-fluorophenyl]propanoate (0.40 g, 0.77 mmol) in a mixture of methanol (4.0 mL) and tetrahydrofuran (8.0 mL) was added 1 N aqueous sodium hydroxide solution (1.53 mL, 1.53 mmol), and the mixture was stirred at 50° C. for 2 hr. The reaction mixture was neutralized with 1 N hydrochloric acid, and diluted with ethyl acetate, and the organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1-hexane/ethyl acetate=1/2) to give a colorless oil. The obtained oil was dissolved in ethyl acetate, and 4 N hydrogen chloride/ethyl acetate solution was added. The precipitated crystals were collected by filtration, washed with ethyl acetate, and dried to give the title compound (0.28 g, yield 70%) as colorless crystals.

後処理

  1. washthe organic layer was washed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1-hexane/ethyl acetate=1/2)
  5. customto give a colorless oil
  6. filtrationThe precipitated crystals were collected by filtration
  7. washwashed with ethyl acetate
  8. customdried

出典と根拠

ORDレコード
ord-ae289b50616a4614a7e800f14306ed35
出典データセット
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07786165B2

反応ノート

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