Citric Acid → 3-(4-{[4-(Diphenylmethoxy)-3-isobutylbenzyl]amino}-2-fluorophenyl)propanoic acid

HRID 508092ノート

反応式

HRID 508092 の反応式
[C:1]1([CH:7]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:8][C:9]2[CH:30]=[CH:29][C:12]([CH2:13][NH:14][C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([O:25]CC)=[O:24])=[C:17]([F:28])[CH:16]=3)=[CH:11][C:10]=2[CH2:31][CH:32]([CH3:34])[CH3:33])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.O1CCCC1>[C:35]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:8][C:9]2[CH:30]=[CH:29][C:12]([CH2:13][NH:14][C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[C:17]([F:28])[CH:16]=3)=[CH:11][C:10]=2[CH2:31][CH:32]([CH3:33])[CH3:34])[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

参加物

7

反応物 4

HCID 311Citric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 23157631Ethyl 3-(4-{[4-(diphenylmethoxy)-3-isobutylbenzyl]amino}-2-fluorophenyl)propanoate

生成物 1

HCID 231572213-(4-{[4-(Diphenylmethoxy)-3-isobutylbenzyl]amino}-2-fluorophenyl)propanoic acid収率 75%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of ethyl 3-(4-{[4-(diphenylmethoxy)-3-isobutylbenzyl]amino}-2-fluorophenyl)propanoate (0.50 g, 0.93 mmol) in a mixture of methanol (8 mL) and tetrahydrofuran (8 mL) was added an aqueous solution (4 mL) of 85% potassium hydroxide (0.20 g, 3.03 mmol), and the mixture was stirred at room temperature for 18 hr. Water was added to the reaction mixture, and the mixture was weakly acidified with 10% aqueous citric acid solution and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was recrystallized from ethyl acetate-diethyl ether to give the title compound (354 mg, yield 75%) as colorless prism crystals.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was recrystallized from ethyl acetate-diethyl ether

出典と根拠

ORDレコード
ord-6044eade1a394e27a6fe983d9909672d
出典データセット
uspto-grants-2010_08
特許番号
US07786165B2

反応ノート

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