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Acetic Acid → 3-[3'-(3-Heptyl-1-methylureido)-2-methylbiphenyl-4-yl]propanoic acid

HRID 250863
ノート
印刷プレビュー

反応式

HRID 250863 の反応式
[OH-].[Na+].[CH3:3][N:4]([C:17]1[CH:18]=[C:19]([C:23]2C=CC(CCC(OCC)=O)=[CH:25][CH:24]=2)[CH:20]=[CH:21][CH:22]=1)[C:5]([NH:7][CH2:8][CH2:9][CH2:10][C:11]1C=C[CH:14]=[CH:13][CH:12]=1)=[O:6].O.[C:37]([OH:40])(=[O:39])[CH3:38].O1[CH2:45][CH2:44][CH2:43][CH2:42]1.[CH3:46]O>>[CH2:8]([NH:7][C:5](=[O:6])[N:4]([C:17]1[CH:18]=[C:19]([C:23]2[CH:24]=[CH:25][C:45]([CH2:46][CH2:38][C:37]([OH:40])=[O:39])=[CH:44][C:43]=2[CH3:42])[CH:20]=[CH:21][CH:22]=1)[CH3:3])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 5

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 67272529Ethyl 3-{3'-[1-methyl-3-(3-phenylpropyl)ureido]biphenyl-4-yl}propanoate

生成物 1

HCID 117185193-[3'-(3-Heptyl-1-methylureido)-2-methylbiphenyl-4-yl]propanoic acid収率 55%

実験手順

100 mg (2.5 mmol, 3.2 eq) of sodium hydroxide are added to a solution of 348 mg (0.78 mmol, 1 eq) of ethyl 3-{3′-[1-methyl-3-(3-phenylpropyl)ureido]biphenyl-4-yl}propanoate in 6 ml of a tetrahydrofuran/methanol mixture (8/2). The reaction mixture is stirred at room temperature for 12 hours. The reaction medium is hydrolyzed with water, acidified with acetic acid solution and extracted with ethyl acetate. The organic phases are combined, washed with sodium chloride solution and dried over sodium sulfate. The solvent is evaporated off and the residual oil is chromatographed on silica (7/3 to 1/1 heptane/ethyl acetate). 180 mg of 3-[3′-(3-heptyl-1-methylureido)-2-methylbiphenyl-4-yl]propanoic acid are obtained in the form of a tacky solid. Yield=55%

後処理

  1. extractionextracted with ethyl acetate
  2. washwashed with sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customThe solvent is evaporated off
  5. customthe residual oil is chromatographed on silica (7/3 to 1/1 heptane/ethyl acetate)

出典と根拠

ORDレコード
ord-6f40237e50844070b072f73b0b73b058
出典データセット
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07863332B2

反応ノート

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